


Life For Rent

by Winchest09



Category: Supernatural
Genre: AU, Alternate Universe - Mob, Blow Jobs, Dark Past, Escort, Eventual Smut, F/M, Fingerfucking, Fluff, Masturbation, Oral Sex, Other Additional Tags to Be Added, Public Blow Jobs, Rough Sex, Sex, Shameless Smut, Slow Burn, Smut, Trafficking, Vaginal Fingering, Vaginal Sex, escort reader
Language: English
Status: In-Progress
Published: 2019-05-26
Updated: 2020-03-01
Packaged: 2020-03-19 23:38:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 22
Words: 92,204
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18980701
Author URL: https://archiveofourown.org/users/Winchest09/pseuds/Winchest09
Summary: Y/N can be anyone for a price. Her life is ruled by contracts, men and money. It’s all she knows; countless identities, seedy clients, and strict regulations. She has to obey the rules, but her past is full of secrets and her future is resting in the wrong hands. But will her next client be the same as the rest?





	1. Preview

**Author's Note:**

> This is a preview to my brand new fiction, Life for Rent. 
> 
> I intend on posting the prologue when my other fiction, Shatter Me, has been completed. You can find that here:
> 
> https://archiveofourown.org/works/17534351/chapters/41313821
> 
> I hope you enjoy the preview! If it sounds like something you'll want to read, pop it in your bookmarks!
> 
> Alternatively - find me on tumblr and request to be tagged!
> 
> Enjoy
> 
> \- Winchest09

Dean threw his head back against his office chair, the luxury leather cool against his clammy skin as he took ragged breaths. Waves of euphoria washing over him as her mouth milked his hardened cock. He felt her fingers graze over the skin of his chest, her touch as soft as silk as she moved his crisp white shirt to expose his toned abdomen. Dean fisted her hair in one of his hands, encouraging her to work harder. His other hand gripped hard at the edge of the mahogany desk, knuckles turning white. He concentrated on the feeling, her hot tongue swirling around the head, the way the sound of her moans vibrated against his cock, the way she took all of him without a gag or a splutter; it took every ounce of control he had to not cum inside her pleasing mouth.

He bowed his head to look down at her. He watched how some saliva escaped from her pretty lips as she bobbed her head down his shaft. One of her delicate hands wrapped around his thick base, the other massaging his balls as she worked. He wasn’t going to cum like this and the tug on Y/N’s hair let her know that. With a reluctant pop, she released his cock from her mouth but not before using her tongue to slowly lap up the moisture she had left behind. Dean growled, his eyes catching hers as he watched her plump lips suck what cum he had just leaked from his tip.

Dean leant forward and grabbed Y/N by the tops of the arms, roughly pulling her up to adorn his lap. He wrapped her legs over him, his cock nudging at her cloth covered entrance as he attacked her lips with his own. Her hands clawed at his hair as he massaged her lips with his own, his hands making light work of the clasp of her bra. Pulling back from the kiss, he took a moment to drink Y/N in, slowly lowering each strap of her bra down her arms, releasing her breasts from their confines. With a smug grin, Dean threw the garment behind him, his tongue coming out to run along the bottom of his lip.

“Y/N,” he husked, taking her breasts into his hands and kneading them. “This is definitely one way to break your contract,” he continued, his lips grazing the nape of her neck, “and to think I almost didn’t hire you.”


	2. Prologue

**Notes for the Chapter:**

> Welcome to my brand new fiction! I hope you’re buckled in because it’s going to be a wild ride! This is just the beginning ;) 
> 
> Thank you so much for clicking on this and for wanting to read. If you have the time, feedback means the world. 
> 
> Here we go!
> 
> -Winchest09

The room was covered in frames and frames of random sketches, doodles and symbols. Some tribal, some mandarin and some Y/N only assumed were from some sort of satanic book. She nervously tapped her feet against the dirty cream coloured tiles as she held her hands in fists on her lap. The faint sound of buzzing could be heard from the rooms upstairs as she awaited her turn.

Today was Y/N’s twenty first birthday and it was a day she had dreaded. Looking to her right, waiting by the connecting door to the upstairs rooms, her watcher stood guard to ensure she didn’t flee. A mere grunt for the master that had orchestrated this whole appointment. Unlike other customers that were currently waiting on the cheap plastic covered seats, making their decisions, her choice of design had already been made for her. It had been handed to the grunt who in turn had handed it to the tattooist as he called Y/N’s name.

With obedience, she stood. The grunt moving to one side, allowing her to pass to climb the chipped wooden stairs before following closely behind her. Y/N followed the tattooist into his room, sitting on the plastic chair the man referenced to. Gingerly she sat, taking in key facts around the room as she waited. The bin overflowing with paper towels and used transfers, the blind in the window broken from misuse and heavy handedness, the ink that stained the surface of the tattooists working area.

Y/N took a moment to glance at the man who would be permanently marking her skin. His skin like an artist’s canvas, different symbols were inked on his arms, the hounds of hades covered his neck. Fitting, she thought. Considering who he was working for. The tattooist turned to look at her and motioned for her to move the hair from the base of her neck. This wasn’t his first rodeo, no words needed to be exchanged between the pair. Y/N just sighed and closed her eyes before feeling the first burn of the hot needle that pierced her skin. She winced slightly but as soon as it had started, it had finished.

The tattooist cleaned and placed a covering over her freshly tattooed neck before ushering her out of the chair. With a nod, her watcher handed a brown packet full of cash over to the tattooist. An exchange that had happened numerous times before. A large hand gripped Y/N’s wrist, guiding her back down the stairs and out through the front door into the street. There, a black hummer H2 4 x 4 was waiting for her. The driver, another expendable grunt, sat there waiting and gave an acknowledgeable nod towards his colleague as he ushered Y/N into the back.

Y/N just did as she was told, there was no point trying to fight it. She had done that a few other times before and she had always paid the price. So there she sat, an obedient little pawn on somebody else’s chessboard. She felt the engine roar, the vibration shaking the windows as she was chauffeured back to her confinement. The drive was short of course, her master never liking any one of his girls gone for too long without his permission or a stack of dollars in his pocket. She sighed heavily at the thought, now she was twenty one, she was too start earning her keep or her life would be on the line.

The hummer pulled up in front of her masters’ luxury building. What once was a hotel for many tourists and visitors from around the world was now a twelve storey beehive for him and his business. A business that involved women, becoming whoever they were needed to be. Y/N looked up at the sign that hung above the double revolving doors. The Hemlock. She scoffed, fitting that her master would name his home after a poisonous plant.

As she made her way through the lobby of the building, heels clicking on the marble floor, Y/N knew all eyes were on her. Word got around this establishment quite quickly. She passed women who were whispering, men who were smirking; they all knew where she had just been and what the implication of that was. Pressing the elevator button a few times, she waiting with her arms crossed to get back to her apartment. When the doors opened, she was greeted with yet more whispers and pointed looks. Y/N just rolled her eyes, it was nothing new in this life so it shouldn’t be such a shock to them.

Reaching her apartment, Y/N let her shoulders relax a little as she put her key in the door. Everything behind this door was just for her. She didn’t have much in the way of belongings. Her clothes were bought for her, so was the furniture, the jewellery, make up and pretty much everything else she needed. But Y/N had a percentage of things that were just hers. Things she had smuggled in and hidden, things from her past she had kept safe, away from prying eyes. She often wondered what it would be like to go shopping, perusing each aisle of clothing, trying them on to see if they fitted right. She often wondered about going out to eat in fancy restaurants or even grabbing something quick from a local takeout. Her meals were prepped and delivered to her door, if she didn’t like what was on the menu, she didn’t eat.

Y/N had not been inside even two minutes when two loud knocks sounded on her door and she cursed under her breath. Opening the big reddened wooden door a crack, she peered at the man waiting in the hall. Dressed in a sharp suit, black shirt with a smarmy smile on his face was another one of the master’s grunts. He forced Y/N’s door wider, not allowing her to hide away.

“He wants to see you,” was his only statement as he folded his arms in front of him, nodding towards the elevator. Y/N simply nodded, grabbing her key card and placing it in her back pocket. She didn’t have to turn around to know that the man was following her closely, escorting her behind the heavy metal doors before pressing the penthouse button.

Y/N’s stomach was in knots. It wasn’t often she went to the penthouse but when she did, it was normally because she had either done something very wrong, or very right. Each outcome made her skin crawl. Taking a deep breath, she collected herself as she watched the little white buttons glow with each floor she climbed. Once the penthouse symbol lit up, she took one last deep breath before the metal doors slid open, revealing her master.

There he stood, two members of security standing either side of him as he took in every single detail about Y/N. His blue eyes slowly inching upward from her legs until his gaze finally met hers. He smirked a little, moving closer to the young girl currently standing in his elevator as he beckoned her to step closer to him. A move that she had to obey.

“My, my, my. What a pleasant day this is turning out to be,” he almost sang as he waved off his security, “don’t turn twenty one every day do we my dear?” he questioned as he leant forward next to Y/N’s ear. She shuddered, feeling his warm breath tickle her skin.

“No, Alastair-” she slipped up, her eyes went wide, “-Sir. No Sir,” she quickly corrected, squeezing her eyes shut in hopes that Alastair, her master, wouldn’t punish her too harshly. Y/N felt how he had stopped behind her, his tongue clicking against his teeth.

“I’ll let you off of that slip up considering it’s such a…special occasion,” he drawled before placing his long, cool fingers against Y/N’s neck. He moved her hair to the side before pulling away the covering of the tattoo, a smirk pulling against his lips, “mmm. Very nice. Always admire Roddy’s handiwork, it’s very…delicate. Do you like it?” He whispered in her ear and she had to swallow the bile that had risen in her throat.

“I…I’ve not had the chance-”

“Oh you’ve not seen it? Well come here my dear, turn around,” Alastair interrupted enthusiastically, taking Y/N by the arms and forcing her to stand in front of the floor length mirror. He smiled over her shoulder, showing some yellowing teeth as he picked up a smaller mirror from his desk. Y/N just watched his movements through the reflection, too nervous to turn around or go against his will. She watched how he held the mirror up to her neck, the reflection of the tattoo showing in the mirror in front of her.

There it was, her branding. The number 128 and a small hemlock flower. She was number 128. The amount of women he had controlled, he had bought and then sold, was terrifying. It took all she had not to cry, it took all she had to not scream till her lungs burned. She wanted to reach for something heavy, hit Alastair over the head and run away but she knew she couldn’t. He was always too quick, he was always too smart, and he was always one step ahead of her.

“Pretty hmm?” he stated, running his fingers over the fresh ink. He let his fingers linger for a moment, his eyes catching hers in the mirror before placing the smaller mirror back on his desk. “Tell me Y/N, how long have you been in my care for?”

“15 years, Sir” Y/N answered without hesitation. Alastair nodded, a sly grin appearing on his cracked lips once more as he looked back at her reflection.

“Oh that’s right. Your daddy didn’t want you, so he gave you to me. His loss, my…gain,” he said gleefully and it made her skin crawl.

“Yes…Sir” Y/N answered, trying to hide her anger, trying to hide her disgust. Alastair just grinned, taking delight in her reaction. He shimmied his shoulders slightly, shaking his body as he let out a chuckle.

“Mmm it makes me all tingly when a new girl becomes available. The excitement, the prospects. I have high hopes for you Y/N,” he sang, pointing his finger at her through the mirror. 

She watched as Alastair made his way around his desk, sitting himself in his big luxurious office chair as he bent his fingers towards Y/N beckoning her over. With a nod, she did as she was told, taking her place in front of him. As she stood, Alastair picked up a black plastic folder, a few white pages bulking the inside as he tossed it on the wood in front of her.

“Your first client. Study. You’re leaving with him tomorrow at 8am sharp,” he commanded and Y/N’s eyes went wide. It was too soon. She’d only just turned twenty one, she couldn’t do this, and she wasn’t ready. She went to protest, her body taking a small step away from him.

“-but Al-Sir it’s-”

“DON’T DISOBEY ME CHILD!” Alastair roared, his fingers playing with the ornamental blade that rested on the edge of his workspace. “Unless you want to spend yet another week in isolation, I suggest you take that folder,” he threatened, pointing at the black plastic on the desk in front of Y/N. She flinched, her stomach flipping at the thought of what he could do with the metal between his fingers. There was nothing she could do about this situation. She could only submit and obey.

“Yes Sir.”


	3. Chapter One

**Notes for the Chapter:**

> Welcome to Chapter One of Life for Rent! I hope you enjoy! If you have time, i'd love to hear your feedback :) 
> 
> -Winchest09

Six Years Later:

Dean’s eyes were screwed up tight, his tongue peeking out slightly over his bottom lip as he focused on the feeling of being balls deep inside of her. His hand was holding onto one of her slender hips, the other hooking itself over her shoulder to hold her in place as he buried himself to the hilt inside. Dean followed the curve of the woman’s back with his palm before landing one slap across one of her pert ass cheeks, earning him a squeal in delight. He smirked, his fingers denting the skin of her hips as he picked up the pace with his thrusts, only for them to falter slightly when two loud knocks sounded his heavy oak wood bedroom door.

“Dean we need to talk,” Sam stated loudly, his tone stern and his voice deep. Dean rolled his eyes as the woman beneath him started to squirm. He withdrew from her, grabbing her by her ankles and flipping her over before encouraging her to sit up. He placed one hand on the back of her head, the other on his cock as he guided it towards her gloss smeared lips, slowly sliding his hard length into her accommodating mouth. 

“Sammy…little busy,” was Dean’s breathless response, as he began to fuck her mouth, trying hard to not lose his rhythm as he chased his delirium. Sam was relentless however, not one for taking any of his brother’s bullshit, he banged on the door again.

“Now Dean!” Sam bellowed, banging once again on the door for good measure to which Dean growled in annoyance.

“Alright, alright!” Dean spat, withdrawing his cock from the woman’s mouth, excess saliva running from her lips to her chin as he did so, “sorry doll, party’s on hold, I’ll find you later.” Dean smirked, using his thumb to skim over her bottom lip.

He watched how she nodded obediently before grabbing her panties from the side of the room and shimming them back up her legs, a sultry look on her face as she did so, her dark hair flipping over her shoulders. He tucked his now softening cock into his boxers before pulling on some suit pants and grabbing at his white shirt as he ushered his latest conquest out of his room. Every day was the same for Dean, his afternoon delight included a fine glass of whiskey and his latest woman tangled between his sheets.

Pulling open his oak door, he was greeted with the disapproving look of his younger brother, leaning against the door frame with his arms crossed against his broad chest. The brunette looked up at Sam, a slight blush on her cheeks as Dean landed a quick slap on her pert ass, encouraging her to quickly run off down the corridor in nothing but her underwear. He turned back to look at Sam, the smirk still on his lips as Sam shook his head at him, pushing off the door frame.

“Really? You couldn’t have at least given her your robe?” Sam chided, his expression unimpressed as he looked down on Dean.

“What do you want Sam?” Dean shot back after rolling his eyes, tired of hearing the same old lecture. Sam puffed out his chest in frustration at his brother’s nonchalant attitude before letting out a long sigh.

“The deal didn’t happen,” Sam muttered quickly, looking Dean dead in the eye as his expression changed suddenly. Sam watched how Dean’s face became one of stone, his eyes hardened as he began to do up the buttons on his shirt. This was not the news he had been expecting nor was it news that he wanted.

“I’ll meet you and the boys in my office, five minutes,” Dean commanded as he stormed off in the opposite direction from his brother, shaking his head slightly as he did so. This was all he needed, it was another blow to his ego, another blow to the Winchester reputation.

Dean slammed the door open to his office and made his way behind his desk, grabbing the crystal decanter that was full of his favourite whiskey and poured himself a glass. He rubbed at his face in frustration before downing the amber liquid in one, hissing slightly at the burn before reaching for the decanter once again. As he was pouring his second drink, he heard the shuffling feet of company on his wood flooring which encouraged him to look up from his pouring. In his office stood two of his most trusted friends, Benny and Cas, followed by Sam who shut the door behind them.

“What happened?” Dean questioned, walking around to the front of his desk to perch himself there, glass in hand. He watched how Cas and Benny looked between each other before Benny took a step forward.

“Boss, they didn’t want to make a deal with the Winchesters,” Benny confessed, his hands at his sides. Dean rubbed at his brow, clearly annoyed at this admission.

“This was a routine deal, we make the same fuckin’ deal every couple of months, what’s the issue?” Dean snapped, his fuse getting short as he looked at his two henchmen, wanting answers. Castiel scratched at the back of his neck awkwardly, ruffling his dark hair as he tried to explain the reason as best as he could.

“It’s, uhhh, well-”

“-it’s you Dean.” Sam cut off Castiel’s ramblings, his tone sharp as he looked at Dean, exasperated. Dean just frowned before raising his brows at his brother.

“Excuse me?” He fired back as he stood of the desk, pointing one finger at his brother. Sam held his ground as Dean walked towards him as he started to explain.

“Crowley and his minions won’t do a deal with us because they’re worried that someone is going to rat them out to the authorities,” Sam disclosed as he wore a pissed off expression. “Tell me, what would give them that idea?” Dean just hung his head in annoyance before he downed his second glass of whiskey.

“Sam, I let my guard down one time,” he reaffirmed, holding up one finger but Sam was just shaking his head, his lips in a thin line as he stared down his brother.

“No Dean, it wasn’t just one time. You always let your guard down when your dick is wet,” Sam chided, running his large hand through his chestnut locks in frustration. Benny and Castiel decided to take a step back when they saw things starting to heat up between the brothers, knowing that it could get messy.

“It’s not my fault that Cassie was a fucking whore!” Dean roared, throwing his empty glass across the room, it smashing on impact against the mahogany bookcases.

“No but it’s your fault for leaving valuable documents out for everyone to see, for anyone to take. Just like she did,” Sam continued pushing, unphased at Dean’s actions, “and what about that Kaley girl and her friend Ruth? If it wasn’t for Benny overhearing them plotting to go to the police with what they had on you, we would be in even more shit!” Sam fired back, motioning one hand to the southern henchman standing behind him.

“Those two were dealt with,” Dean snarled, his lip curling up slightly in anger as Sam sighed, pinching the bridge of his nose.

“Ok so you dealt with the situation but it was your mess to clean up,” Sam shot back, pointing an accusatory finger at his big brother. “What’s it going to take to get through to you Dean? Our reputation is being battered because you can’t keep your dick in your pants for longer than a day. You need to fix this. Dad left the family business in your hands and I’m sick of being the one to pick up the shitty pieces!” With that, Sam turned on his heel and stormed out of the office, leaving Benny and Castiel with Dean.

The eldest Winchester knew that if Sam hadn’t have left, they would have ended up in a brawl which is the last thing they needed right now. He knew Sam was right, Sam was nearly always right and it infuriated him to no end. Dean turned around and leaned on his desk, looking out of the big floor length window which overlooked the gardens. His breathing was deep and slow, he was trying his best to remain calm.

“Can one of you please escort Emma, Emily, Emilia, whatever her name is off this property, along with her friends. Do a full search of each one and then ensure that they do not utter a word of what they have seen in this place. Understood?” Dean commanded without looking over his shoulder, his voice low and authoritative.

“Yes boss,” came Benny’s reply shortly followed by the click of Dean’s office door. Upon that sound, Dean let his shoulders sag as he sighed deeply, reaching once again for the decanter and a fresh glass, pouring himself his third shot of alcohol. He moved around the back of his desk and slumped himself into his plush leather chair, leaning back with a finger pressed against his temple. As he brought the glass to his lips, his green eyes fell on a photo frame that contained a picture of his parents. Everything changed when they were assassinated by a member of the rival clan. An assassin that was still living his life. A year ago, The Winchesters were to be feared, they were respected. Business was good, trade was good and money was rolling in by the millions. Now, they may as well be at the bottom of the pecking order. Dean knew he had a hand in the undoing of it all, Sam spoke the truth with his words and Dean just threw his head back in annoyance. He needed a game plan, he needed to build The Winchester’s reputation up again; he needed to make his parents proud.

As he swilled the whiskey around his glass, Dean’s thoughts were on the upcoming ‘Grande Gala’ that was happening in two weeks’ time. It was an annual event, where all clans came together to speak business, launder some money and walk away with new deals. There was a strict ‘no violence’ policy put in place, not that everyone stuck to it but those that didn’t were never invited back to the following years Gala…and that was bad for business.

“Hey who died?” Gabriel’s question cut through Dean’s thoughts and he looked up from behind his desk frowning at his cousin.

“What do you want Gabe?” Dean sighed, clearly annoyed at the intrusion as he leant forward onto his mahogany desk, swilling the remaining whiskey around in his glass. Gabriel just frowned as he sauntered over to the leather arm chairs facing Dean.

“Who pissed on your pancakes?” Gabriel questioned as he placed himself down in the plush leather, his hands tapping against the arm rests. Dean rolled his eyes before downing the remainder of his glass once again, pushing the glass tumbler along with wood with his fingers.

“The deal with Crowley went south, he called off the trade,” he explained, reaching once again for the decanter only to offer his cousin a beverage. Gabriel nodded and held his hand out to graciously accept the whiskey in the empty glass he had acquired.

“I heard,” Gabriel stated, nodding his head slightly and Dean sighed, pouring the whiskey into his glass before refilling his own. The green eyed Winchester leaned back into his leather chair as he ran a hand through his hair, his focus on his cousin that was currently nursing his glass.

“We use to be feared, respected. Anyone and everyone wanted to be our allies and if they weren’t that, then they sure as hell wanted to ensure they were on our good side,” Dean mused before he clicked his tongue against his teeth as he pondered, shaking his head slightly, “and before you even start, I know it’s on me,” he admitted, staring down into his glass. “We’ve got the Grande Gala coming up in two weeks and I need a plan, I’m not having the Winchester name slandered no more.”

“Dean,” Gabriel sighed, leaning forward in his chair, “as much as I love my women and their sweet delectable little-” Dean deadpanned his cousin, cutting off his speech before Gabriel cleared his throat to continue, “-it’s obviously your weak point. You love your women and I respect that. So here’s what I’m thinking, you turn your weakness into a strength,” he advised as he took a sip of his drink. Dean’s expression hadn’t changed, he was clearly waiting for Gabriel to continue.

“Are you getting to a point?” Dean frowned slightly, encouraging Gabriel to be more forthcoming. His cousin just held up one finger as placed his whiskey tumbler on Dean’s desk before he started to rummage in the inner pockets of his suits lining. After thirty seconds and an ‘ah’ from Gabriel, he pulled out a small business card and slid it over to Dean on the desk, tapping it with two fingers. Dean raised one brow and picked the card up and held hit between his thumb and forefinger.

“The Hemlock?” Dean questioned, clearly confused at what Gabriel was trying to get at. His cousin just rolled his eyes as he picked his drink back up off the desk, falling back into the leather arm chair.

“Oh come on Dean, you’ve heard of The Hemlock surely!” Gabriel replied, the disbelief evident in his features.

“Gabe, it’s your job to know things, not mine,” Dean retorted, shaking his head, the card still between his fingers. Gabriel leant forward once more, wiggling his eyebrows slightly as if he was about to reveal a sordid secret.

“It’s a highly ranked escort establishment, invitation only.” With those words, Dean choked slightly on his whiskey, the liquid burning his throat as he spluttered slightly. He was not expecting those words to leave his mouth at all.

“Escorts? Really Gabe?” Dean chided, shaking his head as Gabriel held up his hands.

“Hear me out. These girls aren’t just like any ordinary escorts. If you want them to be a Russian ballerina, the women will be just that. You want your girl to be all into politics, she will know every bloody thing that she needs too. Hear what I’m saying?” Gabriel asked as he ran his tongue over his teeth.

“Yeah, you’re clearly into some very questionable role play,” Dean retorted, tapping the business card against the desk, running his fingers down the edges. Gabriel just rolled his eyes and leant forward onto his knees, cupping his glass with both hands.

“No-look. Everyone knows you like your women Dean, it’s what got you into this pickle in the first place. So why not get yourself a woman who knows everything about our kinda business, who you’d be able to trust, who would be locked into a contract with you and would be loyal to just you? Take one of them to the Gala, get people back on side. A beautiful, intelligent woman can be more dangerous than a truck load of dynamite,” he advised before taking a sip of his drink. A silence fell over the two men as Dean processed what Gabriel had just said, he did need a game plan for the event. He needed to show that he was someone to be feared, someone that people needed to respect. He needed trade, he needed business and he needed allies. He needed to build his ranks once more if he was going to take down his parents’ assassin in the future. 

“…I don’t know Gabe. It sounds like it could backfire, what’s stopping said woman from blabbing once the contract is finished with?”

“You,” was Gabriel’s simple response, a coy smile on his face. “Look just call Balthazar on that number. He’s my contact in there, keeps his eyes on things for me, he’ll answer any questions you got,” Gabriel explained before standing, downing his drink in one and holding up his glass in thanks before placing it back down on Dean’s desk.

Dean watched as Gabriel left his office, clicking the door shut behind him. He knew he had a point, it would be useful to have a woman on his arm that knew about the business, that was beautiful and intelligent. He smiled slightly as he thought about the relationship between his parents. Sure, his father many have been the don but behind him pulling his strings was his mother, the true don. Smart women in this business were invaluable and hard to come by, many women just interested in the dollar signs and danger.

Dean leant forward on his elbows, fingering the business card as he contemplated Gabriel’s plans. The need to build up The Winchester name was too strong to ignore, he had to gain back what they had lost. With that thought, Dean reached for the phone that was currently being held in its base at the edge of the desk and dialled the number that was on the card. The dial tone sounded for only a few seconds before a greeting was heard on the other end.

“Balthazar, its Dean. Dean Winchester. I’d like to set up a meeting.”


	4. Chapter Two

**Notes for the Chapter:**

> Here is chapter two! Enjoy!
> 
> If you have time, please let me know your thoughts - it means the world to me :) 
> 
> \- Winchest09

Dean’s tan leather suit shoes clicked against the marble floor as he made his way the reception of The Hemlock. His hands in his grey suit pants, his jacket tucked behind his forearms as he walked with confidence towards the dark oak front desk. He nodded in acknowledgement towards the blonde haired receptionist who looked up from her computer screen when she saw the green eyed man approach. He sent her a devilish smile, her cheeks tinging pink when he added an accompanying wink. Dean leaned casually onto the desk, his fingers tapping lightly against the polished wood as he let his eyes roam over the figure of the receptionist, his tongue pulling his bottom lip into his mouth slightly.

“Dean Winchester. Here for a meeting Balthazar. 1pm,” he stated smoothly. Unsurprisingly, thanks to Gabriel’s relationship with Balthazar, Dean had managed to arrange a meeting for the very next day. The receptionist just nodded as she tucked some fallen strands of hair behind her ear.

“Of course Mr Winchester. I’ll let Balthazar know you’re here. One moment please,” she replied politely, if not a little bashful, before making her way to the company phone at the end of the desk.

“Sure honey.” Dean’s smile grew wider as he watched her walk away, his emerald eyes dropping to her ass as she walked. His smile turned into a smirk as he thought of slipping behind the desk and taking the blonde into the back room but the voice of his little brother was still echoing through his head. You can’t keep your dick in your pants for longer than a day. Dean sighed slightly as he turned to face outward into the lobby, he needed to prove a point to his little brother and not let him be right for once.

As Dean stood there, leaning slightly on the desk, he looked around the lobby. There were men of all different ages, styles and character dotted around on the plush seating. He noted the ding of the elevator and observed how a couple of well-manicured women filed out, suitcases rolling behind them before filtering off to their apparent suitors. His thoughts started to wander as he continued to take in all the details of the lobby; the crystal chandeliers, the marble pillars, even the numerous ferns that were planted throughout the area. He was thinking about the conversations from the previous day with Sam and he huffed. If his little brother knew he was here right now, Dean knew he’d be receiving an earful about him being irresponsible with his trust once again but Dean wasn’t going to be fooled this time, and he certainly wasn’t going to jump into any deal head first without thorough planning. Footsteps to his right made him glance over, only to see a tall light haired man wearing a grey v neck t shirt with a suit jacket and pants combo head his way.

“Ah! The infamous Dean Winchester,” Balthazar almost sang, his hands out in front of him. Dean pushed himself off of the desk and held a hand out in greeting.

“Balthazar,” Dean acknowledged, shaking his hand.

“Come, follow me. We’ll talk in my office,” Balthazar proposed, a smile on his face as he approached the eldest Winchester, attempting to snake an arm around his shoulder. However, Dean sidestepped out of his reach, not soliciting the contact before they started to walk back in the direction of which Balthazar came. 

Idle chit chat ensued between the pair as they made the short walk to Balthazar’s office. The door was made from a light coloured wood, the door knob made from what looked like gold which contrasted beautifully against the cream coloured hall. As they entered the room, Balthazar motioned for Dean to take a seat on the opposite side of his birch desk before heading over to the silver tray of alcohol that was neatly arranged on top of some drawers.

“So, how may I be of service Dean?” Balthazar questioned, taking two glasses and pouring whiskey into one before shaking the bottle towards his guest, silently offering him a beverage. Dean just nodded.

“I’ve come to talk business,” Dean replied simply, watching as Balthazar filled up his glass. Placing the glass top back into the whiskey decanter, Balthazar turned to face Dean, a glass of whiskey in each hand.

“Oh and not pleasure? What a shame,” Balthazar witted, a smirk on his lips as he passed the beverage to his guest. Dean rolled his eyes as he accepted the whiskey, bring the glass to his mouth for a quick sip before continuing.

“Gabriel told me about your business, about your escorts,” he stated simply, watching as Balthazar made his way around his birch desk to sit in the white leather chair.

“First of all, not my business nor are they my escorts. I’m just…a keeper of the books,” Balthazar responded, pointing a glass filled hand at Dean, one finger hovering off the glass before proceeding to kick up his feet and rest them on the desk.

“Whatever, alright. I’m just looking to hire one,” Dean asserted, tapping his thumb against the rim of the tumbler in his hand. Balthazar just chuckled.

“From what I hear from Gabriel, you have no trouble in finding your own entertainment. So why would you want to hire one of the girls?” He questioned and he saw how Dean’s demeanour immediately changed. His jaw clenched, his stature become rigid and he leant forward in his seat, locking his eyes with Balthazar’s.

“That’s none of your fuckin’ business Balthazar,” Dean snapped, placing his drink on the edge of the desk before leaning back into his seat, rubbing at his stubble covered jaw.

“Ooh feisty,” Balthazar chuckled before sipping his drink. “Well, if Gabriel has told you anything about The Hemlock, you should know that our girls need to know the reason you’re hiring them, so they can…play the part.” Dean let out a low breath through his nose as he tried to keep his calm. He knew Balthazar was fishing for information and that was something Dean couldn’t afford to give. The Winchester reputation was damaged enough.

“And the woman that I hire will know everything she needs too once she’s on trusted ground,” Dean retorted, his hands clasping together in his lap. 

“Fine,” Balthazar huffed as he pulled his legs off the desk, his hands fumbling with the drawer until his fingers found what he was looking for. He pulled out a thick book, sloppily throwing it onto the wood in front of Dean. “This is the catalogue of all of the girls that are available to go immediately.”

Dean just nodded as he hesitantly picked up the catalogue, his fingers flicking against all the pages to emphasize just how many women were employed here. He looked down at the cover of the catalogue, the casing being made from leather with the hemlock flower imprinted into the material before he flicked to the first page. What he wasn’t expecting was an inventory of women, categorised by body shape, weight, race, hair colour and more. The more pages Dean turned, the more he was starting to feel a tad uncomfortable. He was used to screwing over women, sleeping with them, not calling them back but this felt different. Every now and again he would be greeted with the word ‘RESERVED’ in bright red colouring over a woman’s profile, it made him shift in his seat slightly. These women were basically being treated like they were in a cattle market but what could he do? As he turned the pages of the catalogue, seeing more and more reserved labels on women, he was starting to doubt his plan. He was used to sleeping with women and never calling them back, used to just calling up a fling and having a quick fuck in a hotel room somewhere but he didn’t know if he could bring himself to hire an escort.

Unfortunately, he had no other options or plans in mind. He’d spent most of the previous night trying to think of ways he could manipulate the enemy, thinking of ways he could strike up new deals but he came up with nothing. The only thing that kept circling in his mind was Gabriel’s idea of hiring a woman who could look good on his arm, wow his rivals with her knowledge which in turn would start earning him some respect and help rebuild his reputation. It wasn’t much, but it was a start and he hoped that he could at least give one of these escorts a break away from everything.

“Who would you recommend?” Dean asked as he shut the catalogue with force. No one was jumping out at him, he needed someone special and special meant different to his usual tastes. He just didn’t know what that was and was hoping he would know when he saw her.

“Out of who I have available it would be…” Balthazar leant forward and started flicking through the catalogue himself, looking for Talia, the girl that was popular when others weren’t available. She was fairly new to the business but her skills were rising fast. However, in his peripheral vision, he saw Dean shaking his head. 

“No,” Dean interrupted, “out of everyone, all of the women, even the ones reserved. Who is the best woman on your books?”

“She isn’t available.” Balthazar just shook his head, leaning back in his chair before downing the rest of his whiskey. Dean just growled lowly in annoyance, grabbing his glass back off the desk to finish.

“I don’t fucking care. Answer the damn question,” Dean snapped, he too finishing his whiskey before slamming the glass onto the desk. Balthazar flinched slightly before starting to feel a little intimidated under Dean’s hard stare. With a reluctant grumble, Balthazar reached into his bottom drawer and pulled out a thin folder, sliding it across his desk towards the eldest Winchester, his fingers pinning it to the wood.

“The best woman on our books,” Balthazar sighed, taking his fingers off of the folder. “Meet Y/N. Fluent in all languages, 6 years’ experience in the field, easy on the eye and extremely charismatic. She’s the cream of the crop, the best of the best and she’s fully booked for the next year. You want a woman like that? You need to book her way in advance.” He reiterated his point of Y/N not being available but Dean paid no mind as he picked up the folder and started to turn through the pages.

Dean would be lying if he said he wasn’t a little bit mesmerised by her. Balthazar was right, she was definitely easy on the eye and the next few pages of lingerie shoots made Dean fidget in his seat slightly. She was perfect, she was the one he needed. Y/N was the one that was going to assist him in rebuilding his empire, she was going to be his key in all of this; he just needed to become her client. As he got towards the back pages of her profile, flicking past more boudoir shoots so his cock wouldn’t become hard in company, his eyes landed on her rates. He looked over them once before looking back up at Balthazar.

“That her rate?” Dean questioned, placing the folder down and pointing at the figures inked onto the paper. Balthazar just nodded, his fingers together as he looked on. Dean just smirked, leaning back into his seat with Y/N’s profile in hand. “I’ll double her rates to ensure I have her next.”

“It doesn’t work like that,” Balthazar sighed in annoyance, knowing this was how the conversation was going to go. “The girls have a cooling off period between clients, which allows them to study for their next role. Y/N has studied for her next client and is due to leave tomorrow morning.” Balthazar tried to get his point over as clear as he could but he just frowned when he saw Dean shaking his head.

“Look I need the best of the best. I want this woman, Balthazar. Make it happen.” Dean threw the profile of Y/N back onto the desk in front of him, slapping his fingers down on the paper a few times to reiterate his point. Balthazar just slid the folder towards him before placing it back in the bottom drawer.

“Dean she’s due to leave at 6am tomorrow, what do you want me to do? Ring up the client and tell them that their booking with Y/N has been cancelled due to someone wanting her more?” Balthazar countered, shaking his head as he laced his fingers together on his desk. “All of our clients need her Dean, that’s why they hire her. I-I’m sorry but there are others to choose from. I can recommend-”

“-I’ll triple her rates,” Dean interrupted, opening the inner lining of his jacket to retrieve a thick brown envelope, “give you a little ten thousand thank yous too.” Dean smirked, a knowing look on his face as he wiggled the package containing the money in front of him before throwing it to land smack bang in the middle of the table. He saw how Balthazar’s eyes lit up when they landed on the wad of cash.

“…Dean,” Balthazar warned, albeit pathetically as his eyes hadn’t moved from the pile of notes sat on his desk that had fallen free from the brown bag. Dean just reached back into his suit lining, his hand going in the opposite pocket and pulled out another brown paper bag, tossing it one again in front of Balthazar.

“I’ll add an extra five thousand on top of that if you let me take her now.” Dean knew he had sweetened the deal, money was always a motivator in this business and he knew exactly how to manipulate the situation so he could bring the woman he wanted home with him. Balthazar just eyed up the pile of notes that sat on his desk before sliding them over to himself, opening his own suit jacket to pocket the profit that he had made. Once this had been done, Balthazar leaned over to the silver metal device screwed into the top left corner of his desk and pressed the talk button, allowing some static noise to fill the air. 

“Mike…you there?” Balthazar asked, speaking directly into the microphone of the personalised intercom system that had been wired into his desk.

“Sir?” Was the grunt’s response, his voice slightly robotic as it came through the intercom’s speakers. Balthazar eyed Dean once more before talking back through the microphone.

“Bring Y/N to my office, ensure she brings along her suitcase. It’s an urgent matter,” he stated with authority, not wanting the grunt to ignore his commands or his position within the company.

“Yes Sir.” Mike sounded through the small metal speaker and with that Dean smirked, he had gotten what he wanted without too much of a fight. Without a word, Balthazar stood and poured himself another glass of whiskey, offering Dean the same to toast to their new business arrangement. The Winchester nodded, holding out his empty tumbler and smiled as he watched it get filled. In silence, they both clinked their half full glasses and nodded towards each other in thanks. A new partnership had been made and Dean had a new contact under his belt.

“We need to talk contracts,” Balthazar mumbled, a pen between his lips as he started to meddle around his desk, gathering different pieces of paper.

“Contracts?” Dean questioned, his brow arching as he sipped his drink. The thought of a contract didn’t even cross his mind with this kind of business, he thought you just hired an escort and it was noted down in some book somewhere. Balthazar just looked up at him as he removed the pen from his lips, tapping it slightly against the birch wood desk.

“Dean, you can’t just hire one of our girls without a contract. They have certain rules that they must live by, that they must agree to with each client. We’re not animals,” Balthazar scoffed, that scoff turning into a slight laugh as he held his hands out palms up.

“Look my brother handles that side of things.” Dean brushed over Balthazar’s comment as he leant over the desk and grabbed the few documents that were littered there, his green eyes scanning the pages of the blank contact before rolling them up and tucking them into the inside of his suit jacket. “I’ll have him look this over, we’ll get it filled out and get it back to you.” Balthazar just nodded and twiddled the pen in his hand but a knock sounding at the door caught the attention of both men.

“Come in,” Balthazar commanded and Dean turned in his seat to get a better view of who would be entering the room. As the door opened, the man he could only assume was Mike entered followed by a woman. That woman was Y/N.

Dean let his green eyes roam her figure, from Y/H/C hair all the way down to her ankles, he took in every little thing about her. Her body covered by a little black skater dress, her feet dressed in little black heels. Y/N’s make up was natural, her hair in loose waves and her fingers were bare of polish. Dean let his tongue slide over his bottom lip, pulling it in slightly before smirking. He’d definitely made the right choice. Standing, Dean buttoned up his suit jacket before taking and downing the rest of his whiskey. He walked to Y/N’s side, circling her and placing his hand on the small of her back, smirking towards Balthazar.

“Pleasure doing business with you.”


	5. Chapter Three

**Notes for the Chapter:**

> Hope you enjoy Chapter Three!
> 
> Please, if you have time, let me know your thoughts! 
> 
> Or if you're on tumblr - find me over there too! :D
> 
> Thanks for reading :) 
> 
> \- Winchest09

The lobby echoed with the sound of Y/N’s heeled footsteps as she quickly trotted to keep up with her new clients pace. He held his hand on her lower back, his fingers pressing against her skin as he guided her to the exit of The Hemlock. Her mind was still reeling, this situation had never happened to her. She felt unprepared, overwhelmed and unsafe. It wasn’t the fact that she was leaving with a strange man so soon, she had left The Hemlock with many different types of men over the years but she had always known what she was dealing with first. Her contract had been filled out, their requirements identified and a background check on them completed. This had always allowed her to put necessary plans in place in case anything ever went awry. This time, she had nothing, she didn’t even know his name.

As her client guided her into the revolving doors, he stepped closer to her in order to fit into the same segment. The scent of cedar wood and mint filling her nose as he stood close. Y/N was expecting him to smell like smoke, stale dollar bills and ridiculously overpowered cologne so she was pleasantly surprised to say the least. As they stepped outside, she noticed a black armoured Range Rover parked along the sidewalk and could only assume it belonged to her latest client. As they stepped closer, she noticed the driver’s door start to open, revealing a skinny brown haired man dressed in a black suit and tie. The man that was with her stopped just before they reached him, his palm gestured out wide to his driver as his other hand was still placed at the base of Y/N’s spine.

“Y/N meet Garth, he’s my driver and part of our family. You’ll be seeing a lot of him while you stay with me,” he introduced and Y/N smiled timidly at him, she didn’t really know what to expect just yet.

“Howdy Ma’am, nice to meet you,” Garth greeted with a chirp, saluting two fingers in a chip whilst bowing slightly. Her client just rolled his eyes at his chivalrous ways as Y/N’s smile grew that tiny bit wider.

“Garth…just get her bags,” He sighed, before he opened the back passenger door to the vehicle, nodding for Y/N to get in. She did as she was told and slid into the cool leather to the other side, her legs bare against the material as she sat still in her seat, pulling the seatbelt across her chest.

“Sure thing,” Garth confirmed, hustling around his boss to get Y/N’s bags, placing them carefully in the back. Once he had finished, her new client joined her in the back of the Range Rover as Garth hopped back into the driver’s seat, the engine starting with a thunderous roar.

“We’ll head straight home,” He stated as he looked at Garth through the rear view, he just nodded a confirmation and pulled out into the traffic, his fingers tapping to the wheel to the music humming softly from the radio. Y/N fidgeted in her seat slightly, she wasn’t one to be rude but she had to know what she as dealing with.

“Excuse but may I ask what the job is Mr…” she enquired, leaving her question open for answer as she raised a manicured brow to the man next to her. She saw how he just smiled, rubbing a hand over his chiselled jaw before he replied.

“Don’t worry about the job for now sweetheart,” he drawled, his eyes flickering from hers to admire her body once more, “but the name is Dean. Dean Winchester.” She noted how he didn’t raise a hand for her to shake and she discreetly rolled her eyes. _A man that lacks basic manners_.

“Pleasure,” she spoke as plainly as she could without it coming across as insulting. She hated not knowing what she was walking into, she needed to do her research, and she needed to know what and/or who she would be portraying. Going with the flow wasn’t really Y/N’s style.

As they made their journey back to the Winchester’s home, Dean looked over at the woman that was sat next to him, her hands in her lap as she looked out of the window. She could feel his eyes on her, how they roamed over her figure, taking in everything about her. This was something that she was used to, those lingering stares and the ‘innocent’ touches but she was able to keep her clients under control for the most part. Y/N took a slow deep breath before exhaling through her nose, trying to keep herself calm. She was angry, she had every right to be. For years she had played by the rules, completed everything that was asked of her without a bat of an eyelid, she worked _hard_ to get where she was. So to have Balthazar cancel a booking and just ship her off with a new client within mere minutes made her blood boil. To top it off, her new client had circled around her like a predator stalking its prey. She also knew The Master wouldn’t be very happy with the turn of events either; that thought alone made her shudder.

Her thoughts were broken when she felt a soft tap on her thigh, prompting her to look his way. Dean tried to offer her a reassuring smile but it wasn’t something that was reciprocated. Instead, Y/N’s eyes went wide as the Range Rover turned into the Winchester Estate. She had seen fancy houses before, she had stayed in penthouses and luxurious apartments but this…this was something else. It took thirty seconds for them to drive up the driveway, it snaking around into a half circle as Garth pulled up outside the front steps. Y/N was still looking out the window in awe and it made Dean smirk.

“This will be your home for the next month,” Dean stated as he opened his door, stepping out onto the gravel. She just nodded, her mouth slightly agape as she undid her seatbelt, her car door opening to reveal Dean on the other side. As he opened the door, the momentum allowed his suit jacket to open slightly, revealing to Y/N the pistol that was tucked into his trousers. A 1911 .45 Colt to be exact. _So he’s that type of client._

“Garth get Y/N’s bags then place them in the guest quarters,” Dean commanded, not even giving Garth a second glance as he waited for Y/N to climb out of the Range Rover.

“Sure thing boss,” was Garth’s chipper reply. She hesitantly stepped out onto the gravelled path below, her heels sinking slightly but it was nothing she couldn’t handle. Dean gave her a half smile and nodded his head towards the tall oak double front doors.

“Come,” Dean called and Y/N hid the scowl she wanted to show. She obediently followed him however, her heels clicking against the brick stairs as she climbed the few leading towards the front porch.  

As Dean swung open the front door, Y/N’s eyebrows met her hairline. She knew never to judge a book by its cover but when she first saw Dean, she expected a bachelor pad and the reasons for hire were to make an ex jealous. However it was apparent that he was part of something much bigger and it was something she was not expecting. She continued to follow Dean through the hall and watched when he shrugged off his suit jacket, hanging it on a metal coat stand as he walked past.

“Ok so, basic amenities. This is the kitchen, easy enough to find your way around but we have a chef called Magda that works in the week so she can fix you up with anything you want,” he announced as he walked into the large space, using his hands to motion around everything. Y/N just took it all in, it was huge. Two double standing fridges, two free standing islands, all counter top seemed to be kitted out of black marble. It was beautiful. However, Dean didn’t stop to allow her to look around, he just kept on moving and went out of the side door. It led to an open veranda which was decked out with tables and sofa seating which overlooked a pretty impressive outside pool. He continued to walk until he came to another door, unlocking it with a key and heading inside. This time, he at least held open the door for Y/N to walk through.   

“This is my office, its one place you can find me if you ever need to.” Y/N looked around the space, it seemed a little personal to Dean. She noted photographs on his desk and wall, bookcases filled with literature, it seemed homier somehow but before she could analyse everything, Dean cleared his throat and was standing at the opposite end of the room, to the other adjoining door which she only assumed led back into the house.

No words were spoken as Dean led her through more corridors, she was starting to wonder just how big this place was as she was sure she would get lost if she had to do this on her own anytime soon. As they were just about to reach the stairs to head up to the next level, the double doors to the right of Y/N swung open with a sweaty, taller man stalking out, a towel wrapped around his neck.

“Ah Sammy! Perfect timing, meet Y/N. Sweetheart, this is my younger brother,” Dean introduced, stopping to place one hand on the small of her back again as he grinned towards him. Y/N delicately held out her hand as Sam did the same, shaking each other in greeting.

“Nice to meet you,” Sam replied politely, a small smile on his lips as he looked at her. However that smile soon vanished as he looked down on his brother, “Dean…a word?” Sam spoke through gritted teeth. Dean’s face fell to one of stone and his hand slid from the small of Y/N’s back to her hip, guiding her to the other side of him away from his brother.

“Later Sam, I’m showing our guest to her room,” Dean replied, his tone as venomous as his brother’s as he guided Y/N up the stairs. It was obvious to her that there was some tension between the brothers and she wondered if that was one of the reasons why she was here but judging by Sam’s reaction, she assumed he had no idea what was going on. Dean’s hand stayed on the small of her back along a smaller corridor to an oak door. As he opened it, Y/N was met with an extravagant room. It held a four poster queen size bed, a vanity table, floor length wardrobes and mirrors. As she walked through the room slowly, taking everything in, Dean walked up from behind her and opened up the door to her bathroom.  

“This is the guest quarters. Everything here will be solely yours for your stay and I promise you will have your privacy,” Dean explained as he stood by the bedroom door once more, just watching her take everything in. “You don’t talk much, do you?”

“I’m just being polite,” Y/N answered softly, a gentle shrug of her shoulders. She was good at acting, it was part of her job after all. She didn’t want to let on just how understandably pissed she was. Dean just shook his head as he folded his arms over his shirt covered chest.

“Being polite? I have been speaking to you, without a response, for the past half hour,” he scoffed but Y/N just raised an eyebrow, looking back at him over her shoulder.

“About things that didn’t dignify an answer,” she sassed. She knew she shouldn’t have, it wasn’t what _good girls_ do but she was finding it so very hard to bite her tongue. However, she noted that her response made Dean’s eyebrows meet his hairline in shock, his arms unfolding as he rubbed the back of his neck awkwardly.

“Right, well…” he coughed to clear his throat, “I’ll be back here in the morning, around 11.30am. Give yourself time to get accommodated and preened and whatever else it is you escorts do. I’ll brief you then, you’ll know everything you need to know. Ok?” he asked, his hand resting on the door handle to her room as he looked at her. Y/N just smiled a tight smile.

“Yes, Mr Winchester,” she almost spat upon hearing his words. _Whatever else it is you escorts do._ Y/N was very tempted to throw something at the back of the door that Dean had just closed but her etiquette prevented her from doing so. She had met some arrogant fuckers in her life but Dean had just topped her list. She was used to men speaking down at her, making remarks about what she does, the word ‘slut’ had been used many times with different lowlife clients, but there was something about Dean that was getting under her skin. The way he paraded around the house, the way he spoke about his staff, even the way he spoke to his brother. She took a long deep breath and reminded herself that this was just another job, she would be back at The Hemlock in a months’ time with her next booking and Dean Winchester would long be forgotten. 

Running her hands through her hair, Y/N’s eyes landed on her case that was situated next to her bedroom door. She was going to take a long hot bath and try and relax somewhat before the inevitable meeting with the Dean tomorrow morning. Padding her bare feet through the luxurious thick cream colour carpet, she wrapped her hand around the case handle before ensuring she locked the door, sliding the brass bolt into place. She wanted privacy, she didn’t know these people and considering she spotted a gun tucked into Dean’s trousers, she was going to take all the precautions she could. 

She lifted her case and placed it on the queen sized bed, unzipping it to reveal its contents. Y/N huffed, all the clothes and things she had packed were for the client and job she was meant to be working before Dean swooped in and stole her from under her previous client’s nose. However, there was always one thing that she packed, one thing that was a constant in her life and that was a photo of her and her family. Her mum, dad and her sister. It must have been Christmas as there was a tree in the background all lit up and they were all in pyjamas drinking what looked like hot chocolate. It was a memory that she couldn’t remember but a scenario that she always liked to imagine. She held the photo close to her chest. One day, she thought; one day she will meet them again.

-

As Dean left Y/N in the guest quarters, he made his way back towards his office, stopping off to grab his suit jacket on the way. He knew Sam would be sat in there waiting for him, looking through one of the many literature books on his shelf to keep himself busy. As he made his way closer, Dean undid the buttons on his cuffs, losing his shirt just a little to roll up his sleeves to his elbows. He knew this talk with Sam would be a heated one but this time he was prepared. He opened the door to his office and almost immediately, his little brother had him pinned up against the wall, his forearm across Dean’s chest and he held him place.

“You just don’t fucking learn do you Dean?” Sam spat as he shoved his arm harder into his brothers chest.

“Calm your shit Sammy, it’s not what you think,” Dean grunted as he frowned at Sam. He brought his arms up and managed to push him away, Dean’s statement encouraged Sam to loosen his grip.

“Then please…enlighten me,” Sam replied exasperated, his arms held out to the sides as Dean walked around him to the crystal decanter that sat on his desk.

“She’s an escort-”

“A HOOKER!?” Sam roared. “Wow Dean you’ve really surpassed yourself this time.” Dean flinched at Sam’s tone, rubbing at his forehead as he grabbed a glass and placed it bottom down on the mahogany surface, filling it with whiskey.

“Fuck – just listen ok? Gabe mention-”

“Gabriel!” Sam interrupted, rubbing at his own forehead in frustration. “You’ve taken advice from Gabe? Dean…” he sighed, slumping down into one of the chairs in front of Dean’s desk. Sam couldn’t believe his brothers stupidity. Gabriel was clever, granted and he had useful contacts in many different places but sometimes, his advice wasn’t the greatest.

“Sam, can you stop interrupting me?” Dean chided, his brows creased as he held the decanter in his hand. “Yes she’s an escort but not your everyday escort alright? She can be whoever I want her to be and be pretty convincing with it too,” he justified, placing the decanter down before digging about in his suit jacket and throwing some documents down on the desk in front of Sam. “Also I’ve not hired her for sex, I’ve hired her for information and to help get us close to the enemy.” Dean moved to sit down in his leather chair, leaning back slightly as he sipped on his whiskey.  

“How?” Sam questioned, leaning forward with a doubtful look on his face. Dean just smiled, swilling the liquid around in his glass as he thought of the plan that had formulated in his mind.

“Think of the roles she’s had to portray, the people she’s gotten close to. Think of all the information she’s going to have locked away in that pretty little head of hers,” he explained, using his free hand to tap his head with his fingers. Sam just shook his head once more in disbelief, his brown locks falling about his face as he did so.

“And how many of those men will recognise her face?” Sam blurted out as he stood up from his seat, annoyed that once again his brother didn’t see the loop hole. “You didn’t think of that did you?”

 “Sammy…just fucking trust me on this alright? See for yourself.” He motioned towards the documents on his desk, the catalogue he had previously looked through which was left open on Y/N’s page and the contract Balthazar had given him. Dean leant forward onto his desk, pointing down at the papers, “I’ll also need you to go over that contract as I need to send a copy back to Balthazar tomorrow.”

Sam didn’t say anything. He just stood there staring down at his brother before snatching the documents off Dean’s desk and making his way out of the office. As he shut the door behind him, he took a deep breath to try and calm down. He didn’t want to fall out with Dean, if anything, he wanted his plan to work but at this moment in time, Sam didn’t see how having an escort living under their roof was going to help anything. The youngest Winchester looked down at the documents in his hands before folding up the catalogue, not wanting to look at any of the women that were being sold. He flicked through the papers to find the contract and he let out a groan. It was 11 pages long. With a sigh, Sam slapped the documents against his hand and made his way to his own room.  

“Just what have you gotten us into this time Dean?”


	6. Chapter Four

**Notes for the Chapter:**

> Thank you to everyone who reads this. If you could leave a comment or let me know your thoughts, i'd really appreciate it! 
> 
> Find me on tumblr - Winchest09

Dean leisurely strolled down the hallway, fiddling with the collar of his white cotton shirt. His sleeves were folded to his elbows and a few buttons were undone for a more casual look. However, he still donned his suit pants and tan leather shoes. He was making his way to the guest quarters, a new day meant new possibilities and he was eager to start working on his plans and putting things in place. That meant working with Y/N, briefing her on what was to come and ensuring she knew all there was to know about his world.

He brought his knuckles up to rasp on her wooden door softly, leaning his head to listen out for her footsteps as she padded closer towards him. He heard the lock undo before the handle jiggled, the door opening ajar just enough for her to peek to see who it was. When her eyes landed on Dean’s, she smiled politely and opened the door fully. He had to take a moment to appreciate her, her make-up was natural and her hair was plaited neatly into a fishtail braid. She was wearing another little black dress, this time it was more fitted with lace sleeves and a little black bow on the front. Y/N looked breath-taking but then again, that was her job.

“Morning sweetheart,” Dean chirped, a small smile on his lips as Y/N moved to the side to allow him into her room. “You get the breakfast I sent up?” he asked, his hands in his pockets as he watched her fiddle with the lace sleeves of her dress.

“I did thank you,” she replied politely, closing the door softly before walking over to the vanity desk that was placed in the room.

“Magda makes the best pancakes and bacon huh?” Dean mentioned, his question rhetorical as he perched himself on the end of the queen sized bed. Y/N shook her head slightly as she raised her shoulders, checking her reflection in the mirror.

“Oh…I didn’t try them. I had the fruit instead,” she spoke quietly and Dean noted the lack of enthusiasm in her tone, it made him sit up straighter, his eyes never leaving her reflection.

“Really? Fruit over pancakes?” he questioned as he raised his brow, not understanding how anyone could turn down bacon and pancakes for breakfast. He noted how Y/N’s body sunk into itself slightly before she turned to face him on her stool, a binding of documents in her hand.

“I just like to be healthy.” Y/N shrugged before standing and making her way over to him.

“Hm. You and Sam will get along famously,” Dean muttered as he rolled his eyes.

“I need to give you this,” Y/N stated, partly shoving the binding document into Dean’s hands as she stood before him with her arms by her sides. “It’s like my own little welcome pack. It’s got everything in there that you may possibly want to know. Latest medical documents, allergies, a full health check-”

“Oh sweetheart, I don’t do reading,” Dean laughed through his nose as he shook his head, placing the ‘welcome pack’ onto the bed next to him. He didn’t see it but Y/N rolled her eyes at his defiance before continuing with her explanation after he interrupted her. 

“It also has a list of all of my aliases with matching photos. I like to keep up to date with them so if a client ever needs to revisit a role, my alias is quick to put together,” she explained, using her hands to talk at the same time. She saw how Dean’s demeanour changed when she confessed what else was inside, his eyebrows raising slowly.

“That so?” he questioned, pursing his lips together as he started to peek through the pages. “Maybe I’ll take a glance,” he confessed, standing and picking the welcome pack up with him.

“You do that,” was Y/N’s simple reply as she slipped her feet into her black heels, a little sigh passing her lips. Dean frowned when he heard the little sound escape her, he almost wanted to ask her what it was about but decided against it. Instead he checked his watch and headed over to the guest room door, opening it up and waited patiently.

“Shall we?” Dean motioned towards the open door, one hand resting on the door handle as his emerald eyes caught Y/N’s gaze. She just nodded and walked out of the room, her hands clasped together in front of her, her head turning to look all around her as she waiting for Dean to lead the way. He gestured for her to follow him and she nodded simply, a small smile on her lips as she did so. He noted that she wasn’t walking beside him, even when he slowed his pace she kept behind him and it was something that he would bring up at a later date. He wanted her at his side, not following him like some sort of shadow.

Dean made his way down a new set of corridors, ones that he had not shown Y/N the previous night. In his peripheral vision, he saw how she was looking around at the photos on the walls and the artwork she was passing. He was leading them to Sam’s office on the other side of the estate, it was closer to the library as Sam just loved his literature. Dean checked his watch again as he approached his little brother’s office, knowing full well that he would already be waiting inside. He was hoping that he had calmed down some from the previous night. He was hoping that Sam had gone over the documents he had given him and put some thought into his plan. He needed his little brother to be on his side, he needed this to work for both their sakes; for the family’s sake. Dean knocked twice before turning the gold door handle to reveal Sam’s office and sure enough, his little brother was sat behind his desk.

Dean nodded for Y/N to enter and watched as she looked around the room, taking everything in. Sam’s office was different to his own. The décor was lighter, the furniture was made from birch wood instead of mahogany and there were a few more plants. Two leather couches sat opposite one another to the right and left of the room, a coffee table resting in the middle while Sam’s desk was situated straight ahead. A fern was in the back corner, photo frames and diplomas were nailed on the walls as well as scattered along shelves containing books about law and punishment. Sam looked up from his laptop straight away and stood up in greeting when Y/N entered the room.

“Morning Y/N, how are you?” Sam smiled, messing with the buttons on his suit jacket as he stood. Y/N’s head snapped up immediately to meet his gaze and she smiled.

“I’m fine, thank you Sam,” she replied, appreciating his concern for her welfare. Dean shut the door behind her and made his way to the couch on the right as Sam picked up his laptop and placed it down on the coffee table in the room.

“Please, sit,” Sam gestured towards Y/N, a softness in his features. “Would you like some water?” He questioned as he walked over to the mini fridge that was built into one of the cabinets behind one of the couches.

“Yes please,” she replied politely with a nod of her head as she sat down on the couch next to Dean. Sam pulled out two bottles of water before leaning over the coffee table to hand one of them to Y/N. The other, he then opened and took a generous swig before sitting on the opposite leather couch. Dean just frowned at his little brother, his palms facing upward to gesture his disbelief that Sam didn’t pass him a bottle.

“I’ll get my own then,” he grumbled under his breath with a huff as he pushed himself off of the leather and made his way to the fridge.

“So, we have a lot to discuss it seems,” Sam said confidently, opening his laptop and logging back into his account to reveal a digital copy of a new contract, much like the one Balthazar had passed to Dean the previous day. As Dean turned from the fridge, water in hand, he saw Y/N fiddle with the ends of her hair.

“If you don’t mind, before we get started, I’d really like to know what the job is,” she stated, looking between both brothers. Sam’s face became free of emotion as he turned to his brother, disappointed that he’d left her hanging all this time.

“Dean?” He prompted through gritted teeth and Dean just nodded, leaning back onto the cabinet crossing his legs at his ankles before he started to undo the cap on the bottle.

“We have a Gala that is coming up in just under two weeks, the Grande Gala, and I need you to be my date. I need you to help rebuild my-” Sam cleared his throat and Dean rolled his eyes before he continued, “-our, reputation. Sweet talk my contacts, wow them with your knowledge and help me put people in their places,” he stated before taking a generous mouthful of water. Y/N looked between Dean and Sam, a small frown on her brow. With how mysterious Dean had been with her about everything, she expected something a lot bigger than being his date.

“That’s it?” she questioned, raising one eyebrow as she did so. Dean frowned, his lips straightening in a thin line at her response.

“What do you mean _that’s it_?  he retorted, using his hands to quote what Y/N had said, “it’s a serious job,” he continued, his tone harsh as he circled back around to join her back on the couch but Y/N just shrugged with a nonchalant attitude.

“It sounds like a standard one to me,” she confessed as she played with her own water bottle. It wasn’t just Dean that had caught onto her nonchalant attitude, Sam had as well and he leant forward a little more in his seat, leaning his arms on his knees as he interlinked his fingers.

“Y/N, sorry but may I ask if you know who we are?” Sam questioned, looking briefly over to Dean who was leaning in the corner of the couch, his arm resting on the leather as his hand rubbed at his forehead. Y/N just looked between the brothers once more, not understanding the sudden obvious question.

“Is this a trick question? You’re Sam and he’s Dean, I’m assuming you’re both Winchesters,” she stated, huffing a laugh through her nose before she took a drink from her water, her throat becoming dry.

“Yes…we’re both Winchesters. We’re the head of the Winchester Family,” Sam replied, his thumbs rubbing together as he watched Y/N intently. Dean was beginning to lose his patience, he didn’t have a lot to begin with but this was a sensitive subject. In Dean’s eyes, everybody should know who the Winchesters were.

“Ok,” Y/N stated simply as she placed her water bottle on the coffee table. Sam was unable to respond before his elder brother slapped his hand down hard on the leather couch.

“Seriously?!” Dean raged, shaking his head slightly as he began to rub his finger across his lip in frustration. “Sweetheart you need to be educated in who we are and what we do,” he accused, leaning towards her in a slightly intimidating manner but Y/N didn’t budge.

“I don’t need to be educated in anything,” she retorted back, shaking her head. “You’re the Winchesters. John Winchester was your father and Mary Winchester was your mother. They were both killed by assassination by a rival mob. You, Dean Winchester became the don of the family, naturally as you’re the oldest. You deal with drug trafficking, money laundering and more. I could go on but I won’t,” she explained in a calm tone.

Sam tried his hardest to hide his smirk behind his hands, trying to feign that he was scratching at his stubble. It wasn’t often Dean was put in his place by anyone, let alone a woman, so this was a welcomed change. Dean went from enraged to slightly aroused in seconds, his words becoming jumbled in his mouth.

“How di-how do you know that?” Dean stuttered, clearing his throat to try and regain some composure. Y/N just smiled and shook her head slightly, a little laugh leaving her lips.

“There’s this genius invention called the internet. You just need to know where to look. It’s my job to know who I’m dealing with, to get the facts straight. So I did some research last night after you left me,” she confessed and she heard Sam let out a small laugh in front of her as she dared to meet his hazel eyes.

“We appreciate that Y/N,” Sam admitted, a small smile on his lips. “However there are things on the internet that may not be entirely true. It also doesn’t tell you everything about our family. We will give you some files to go over in time for the Gala if you don’t mind?”

“Of course not.” Y/N shook her head, seeming genuinely happy to go over anything they give them. Dean noted that it appeared she took pride in her work and what she did, it was probably what made her the best of the best and that was something he could respect.

“On that note, let’s go through this contract,” Sam announced, bringing up the documents he needed and pulling out a pen from the inside of his suit pocket.

For the next forty five minutes, Sam read through each section of the contract carefully to both of them. They went over what Dean was to provide for Y/N. Food, toiletries and anything she made need to perform her role to the best of her ability. They also covered her stay within the manor; that the guest quarters were solely hers for the length of her stay and she was promised her privacy, an agreement that Y/N was happy about. It was rare that she got to stay on her own when she was on the job, clients normally making her sleep in the same room as them, a clause they always added to the contract to ensure she couldn’t get out of it.

“This next section explains everything that Y/N has to offer in a…erm…sexual manner,” Sam stated, clearing his throat as he peered over the lid of his laptop. Dean smirked next to Y/N, he couldn’t deny that he loved sex, hell who doesn’t, but his smirk faded when he noticed the slight shuffle Y/N made next to him. To anyone else, it might have been missed but not to him. Even though it was her job, the slight movement that she made paired with her closed off body language indicated to Dean that she was slightly uncomfortable and that concerned him. Sam took a breath to continue, looking at his brother directly.

“So, Dean, do you wish for any of the following sexual services-”

“Strike them all off,” Dean said confidently, leaning forward himself in his chair and looking Sam dead in the eye. Not only did he want to prove to Sam that he was true to his word, he hadn’t hired Y/N for sex, he also did not want to put her in a position she wasn’t entirely happy with. He wasn’t brought up that way. He noted how Y/N snapped her head to look at him, wide eyed in shock, obviously not expecting to hear that answer.

“What?” Sam half laughed in disbelief, not entirely believing that his brother did not want any kind of sexual gratification from the escort but Dean just shook his head as he rubbed his hands together.

“Strike them all off. I told you Sammy, sex isn’t a part of this deal. All I require, along with any information Y/N can give me, will be public displays of affection. Kissing, maybe some light making out, hand holding etcetera to make this look convincing,” he stated, his stare not once leaving his brothers before his face held a softer look as it turned to face the woman sitting next to him. “Is that ok with you Y/N?” He questioned, his tone gentle.

“Yeah it’s f-fine,” she stumbled on her words, her mind still not catching up to the fact that the handsome green eyed man she was employed by only wanted her for her skills and not her body.  

“Good. Let’s move on,” Dean nodded and leant back in his seat. Sam swallowed hard, letting out a small breath as the moment passed.  

“Ok so working hours?” Sam asked, typing away manically on his keyboard.

“Y/N there will be no set hours for this job. It will be as and when I need you. I will give you plenty of notice, is that ok?” Dean questioned the woman next to him who still looked like she was a deer in the headlights.

“Uh-huh,” she agreed, leaning forward to grab her water bottle back off the coffee table to take a sip. Dean clapped his hands together before rubbing them both over his face.  

“Good. Now that’s sorted, I want to edit the client confidentiality part of the contract,” he stated, standing up to walk around next to his little brother, glancing over his shoulder at the contract Sam was currently working on.

“That’s wise,” Sam agreed with a nod of his head before looking over at Y/N. “As you can understand, in our _line_ of work, we need complete anonymity. Now I know it’s stated here that you give that but we are adding a clause that you are not allowed in areas of the house that Dean states are off limits. We are also adding a clause that if you do break our confidentiality agreement, or any of the clauses in this contract, we have the right to resolve it our way,” Sam said clearly and he watched as Y/N frowned.

“What does that mean?” she asked, her tone a little sharp as she looked desperately between the two brothers. Dean just smirked as he walked around to stand in front of her, sitting himself down on the edge of the coffee table to look her dead in the eye.

“It means, you don’t wanna fuck with me sweetheart.” His tone was dangerously sweet, his thumb and forefinger pinching at her chin to encourage her to look him in the eye, “because neither of us will like what happens if you do.” 


	7. Chapter Five

**Notes for the Chapter:**

> Thank you to everyone who reads! I hope you enjoy Chapter Five
> 
> -Winchest09

Y/N followed Dean out of Sam’s office after signing the contracts that the youngest Winchester had freshly printed off. Her mind was still reeling with all of the information they had gone through and Dean’s not so friendly reminder that he was not to be messed with. As she made her way back down the corridors, heading back to the guest wing, she also thought back to Dean’s statement about not wanting any type of sexual contact whatsoever under this agreement. No sex? She frowned as she walked. In her 6 years of actively working as an escort, she had never had a client that didn’t want at least a blowjob from her, this was completely new territory for her to be in.

“So sweetheart, you remember what rooms you’re not allowed to be in?” Dean’s voice cut through her thoughts as she tried to keep up with his strides.

“Your room, Sam’s room, the staff quarters, the boardroom unless I have your permission and the entire basement level,” she relayed back to him, her hands twisting together as she remembered them all. Dean turned as he walked to look at her, one hand in his pocket and the other at his side as he smiled.

“Good,” he praised before stopping at the door of the guest quarters, jiggling the handle and letting himself in. Y/N just stood back and watched for a moment as he casually walked into her, now, private space. She assumed that he wanted to talk business, considering sex was completely off the table at this point, she didn’t understand why he would want to be in her room otherwise. She followed him in and closed the door gently behind her, the latch clicking as she leant her back and hands up against the wood. Dean pulled is hand out of his pocket and pointed towards her closed luggage case at the bottom of the bed. “You not unpacked yet?” He questioned, an eyebrow arching.

“I have a little bit, just not done it all,” she confessed as she walked closer to Dean, “I wanted to spend my free time getting to know my new client,” Y/N countered, a little smile on her lips. Dean laughed through his nose and she saw how his shoulders moved with it. She knew that they already appreciated her efforts and the way Dean smiled at her when he picked up his head to look her way, confirmed it.

“Come on, I’ll help you,” he offered, automatically picking up the handle of the case and laying it on the bed, “let’s get you settled in.” His hands were already searching around the case for the zipper and Y/N eyes went wide.

“Oh n-no it’s fine, don’t worry,” she fussed, rushing over to try and politely usher Dean away from her case. She didn’t know what was going through his head at that particular moment, whether he was just trying to make her feel more comfortable or he was just genuinely trying to be helpful, but she would prefer to unpack herself.

“I insist, doll.” He shook her off as he flipped open the lid. As his olive eyes left hers, they landed on the contents of her case and she saw how the tips of his ears turned a little pink. Y/N bit the corner of her lip to try and stifle a smile. She knew exactly what he was walking into, it was why she wanted to unpack her case herself. He’d found her packed stash of sex toys that her original client had requested. She brought her thumb to her mouth as she watched Dean pull out a small leather piece of bondage equipment, a leather strap attached to a stainless steel ring. “Wh-what is this?” Dean stuttered, hooking his forefinger into the steel ring and lifting it from the case. Y/N just shrugged, coming forward to sit on the edge of the bed just next to where Dean was standing.

“Oh…it’s an adjustable stamina cock ring,” she explained, reaching up to where it was still dangling from his finger, “you put this bit-”

“-I can gather where it goes,” he interrupts, a perplexed look on his face as he continued to study the cock ring, bringing it closer to his face for a better look.

“Why the fascination? You want to try it?” Y/N asked playfully and held back a snort when Dean looked at her wide eyed.

“Oh no sweetheart, I’ve got all the stamina I need thank you,” he retorted, laughing through his nose as he dropped the ring onto the bed next to where Y/N was sitting. She just arched her brow at his response, _I’m sure you do._

“Suit yourself,” she replied, picking up the toy and hooking the leather over her fingers, moving it from side to side. “Don’t knock it ‘til you’ve tried it,” she taunted with a single wiggle of her eyebrows.

“Ok Y/N I gotta ask, what’s with the multiple personalities?” Dean let out a single laugh as he ran one hand down his face, angling his head to look at her.

“What?” she replied, feeling like all of the wind had been knocked out of her sails, her playful smile falling from her lips.

“First you’re full of attitude, then you’re sweet and polite, and now you’re this flirty confident woman,” Dean confronted, calling her out. Y/N just swallowed hard.

“I thought that’s what you wanted. I’m just trying to find out who you need me to be,” she responded, her spark dimming. All that was going through her head was how she had failed her client, and failures meant punishments, punishment by The Master himself.

“I don’t need you to be anyone other than yourself Y/N. I want you to be you,” he replied truthfully, his voice gentle as his features were soft. She tried to force a smile back at him as his response warmed her somewhat but she couldn’t help the panic that was starting to rise up from inside of her at his request. _Be myself. But,_ _I don’t know how to be me._ Nobody has ever given Y/N the option of being herself. She had always needed to be something for someone, be a little more flirty here, a little more quiet there. She could be an Italian artist, a politician’s wife, a Spanish dancer; she could be anything that anyone could ask of her. But being herself was a role that she has never had to portray, her identity had been lost in the countless aliases and identities that she had had over the years.

“Ok.” She nodded, all she could do at this moment was agree with Dean. After all, he was her client and that was what he had requested from her. She watched as his smile grew wider, his large hands dipping back into her luggage case on the bed as he continued to help her unpack.

“Now back to these…” Dean said with a flirtatious grin, pulling out a variety of butt plugs, vibrators and whips, “I definitely know what these do.” He winked at Y/N and she couldn’t help the pull she felt on her lips as she broke out into a smile. She noted how he was naturally flirty, how he took a keen interest in looking at what was in her case as his green orbs glinted with mischief. She decided then and there that she was going to choose a personality that she knew she could portray well, she would pass that off as her being herself and considering Dean was such a natural flirt, she felt it was only right to mirror his behaviour. She stood up to sort through the rest of the toys in her case, lining them all up on the bed.

“Surely Dean Winchester doesn’t need assistance in that department?” she teasingly asked, running her finger over each one of her toys, looking up at him from under her lashes.

“Oh sweetheart, I don’t need any help. I’ve got plenty of ways to drive you wild without these,” he smirked, using his tongue to guide his plump bottom lip between his teeth, “but it never hurts to play.” Dean looked over at Y/N as she let out a small sigh before brushing past him to access her case once again, pulling out her lingerie.

“Shame I won’t get to see what you mean,” she half shrugged, letting her black lace chemise fall against her body, “but it gives me something to think about,” she added seductively, looking down at the lingerie set resting against her. Dean also looked and he felt his mouth go dry. The chemise was a mixture of sheer mesh and lace with a plunging v line, suspender straps hanging from the bottom. Truthfully, it was one of Y/N’s favourite pieces, it made her feel incredibly sexy.

“I…uh…I need to meeting-go,” Dean stumbled over his words before he cleared his throat, “I need to go - I have a meeting,” he corrected, “I’ll catch up with you in a bit.” Y/N looked up from her chemise and watched how Dean practically ran from her room. She couldn’t help the knowing grin that broke out on her face as she began to fold the lingerie. She might not be able to sleep with the gorgeous man, but she could still have a hell of a lot of fun teasing him.

-

Closing the door behind him quickly, Dean rested the back of his head against the wood as he palmed his throbbing erection through his trousers. He was an idiot for thinking this no sex deal was going to work, it hadn’t even been a full day and his cock was already painfully hard, twitching in its confines. He needed release, and he needed it now.

He paced down the corridor away from Y/N’s room, pulling his phone out of his pocket as he did so. He had a list of many different women that he could call, women that would do anything to be fucked by him; women he had met on nights out or that knew that they were just there for a good time. As his finger hovered over the call button on a random number, he tapped the edge of the phone against the side of his head. He couldn’t prove Sammy right, not yet, it had been barely two days since the confrontation with his brother. Grunting in frustration, Dean picked up speed and headed to his bedroom, Y/N had got him in the mood and he was too worked up to think straight. He had to deal with this one way or other.

He entered his room quickly, shutting and locking the door behind him. He was quick to undo his belt and fly, loosening his suit trousers as he walked. He placed himself on his bed, shuffling his boxers down to just below his balls as he released his throbbing erection. His cock was already leaking precum, his balls already aching to be emptied. He sat back against his dark leather headboard, his large hand encasing his cock as he started to think of Y/N. He dipped his thumb in the liquid on his tip as he swirled it around the head, hissing as he did so.

_She stood in front of him as he sat on the end of his bed, the black chemise dropping to the floor in front of her to reveal her luscious body underneath. He wasted no time, his large hands wrapped around her hips as he tugged her towards him. He kissed at her stomach, his tongue chasing his kisses as he worshipped her body with his mouth. His hands left her hips and traced up both of her inner thighs, forcing them to part wider. Once he was happy with how wide she was spread, he moved one hand to grab at her ass while his other cupped at her sex. His fingers dipped through her folds, a growl escaping his lips when he felt how wet she was for him._

Dean began to pump himself hard, his head thrown back as he did so. He started slow at first, enjoying the overwhelming sensation of pleasure but he needed more, he always needed more.

_He wasted no time in dipping his fingers inside of her, hearing how she gasped at the sudden feeling spurred him on more. One finger became two, two became three. He loved how she was responding to his touch, his fingers rhythmically coming in and out of her, hard. She was mewling above him, her hands gripped on his shoulders as he took one of her breasts into his mouth, swirling his tongue around the nipple. He knew she was close, he could feel the way she was clenching around his fingers as he fucked her. He could feel her nails digging into his skin as he continued his relentless assault, her legs were shaking; she just needed that final push. Dean dipped his head, bringing his free hand around to part her folds before allowing his tongue to flick over her clit. She screamed in ecstasy._

“Fuck,” Dean let out a shaky breath as he worked himself hard, the image of her coming undone over his hand made his balls clench. He wondered what she’d taste like, if she sounded like he imagined when she came.

_Picking her up by her thighs, he turned and threw her down onto his bed, landing with her. His lips caught hers in a heated kiss, tongues fighting for dominance before she broke away and gently bit at his lip. He positioned himself between her legs, his hard cock nudging against her entrance as he kissed down between the valley of her breasts. The way she responded to his kisses made his cock twitch. With every one of her moans, he’d throb. He just wanted to feel her warmth wrapped around him. Taking a hardened nipple between his teeth, rolling his tongue over the nub, he reached down and coated his cock in her slick. He allowed himself to settle at her entrance, enjoying how she was mewling underneath him._

Dean was fucking into his hand at the point, his hips jolting off his mattress with fervour. His breathing was ragged, a small sweat appearing on his brow. His tongue pulled in his bottom lip as he tried to keep his breathing under control.

_Letting her nipple go, he ran a hand down her side and lifted her leg to hook it over his arm before he started to push his cock inside of her. He was slow at first, the feeling of being enveloped by her delicious pussy was almost too much to take. He closed his eyes, her velvet insides feeling perfect around him as he snapped his hips forward in one fluid motion, filling her to the hilt. He heard her gasp underneath him, her hands clinging to his bed sheets as she arched her back. He knew she was desperate for him to move, she was clenching around him causing him to let out a low growl. He collapsed into her neck, nibbling and sucking at her soft skin before withdrawing to the tip. As she whimpered at her loss, he thrust hard back down inside of her._

Imagining how she screamed for him, how she moaned for him, made his cock twitch in his hand. He fisted at the sheet next to him as he fucked his hand as hard as he could, he was chasing his delirium; it was so close.  

_Dean started to gain a steady rhythm as he fucked her. However, he felt himself lose control when her hips started snapping to meet his, she felt so go-_

"FUCK!" Dean cried, cum spilling into his hand just as his fantasy was getting started. Panting, he tried to regain his composure, resting his head against the headboard. "Well that was embarrassing," he muttered, reaching over to his nightstand for the tissue to clean himself with. He shook his head with how quickly he came, when he’s had to resort to these drastic measures before, it was always a good ten to fifteen minutes worth of pumping before he found his end. What had Y/N done to him?

Once he was all cleaned up, Dean pulled up his boxers and buckled up his trousers. He could only hope that he didn’t end up in this situation every time he bumped into her, otherwise, this was going to be a very long, frustrating month.

Checking his watch, Dean knew he had to check in with his little brother and knowing him, he would be sitting in the boardroom with his laptop waiting for their men to join them for their latest briefing. Previously, Dean missed these meetings due to being tangled up in the sheets with his latest conquest but considering he was trying to prove a point, he wanted to be present. Half jogging down the corridor, Dean reached the boardroom and pushed open the heavy wooden doors.

“Sammy?!” he called, a teasing smile on his face as he saw his brother at the end of the long oak table. “You got any lotion? I know you moisturise your hands,” he stated, a smirk on his face as he walked towards his brother. Sam looked up from behind his laptop, a frown on his brow as Dean approached him.

“Wha-no not on me,” he answered confused as he leant back in his seat, “since when do you use lotion?” Sam asked, his brow furrowing deeper. Dean just gave him a deadpanned stare as he leant a few fingers on the table, tapping the wood.

"I have a stupidly attractive escort in literally nothing, unloading underwear and sex toys onto a queen size bed, and I’m not allowed to touch her. What do you think I need it for?" he asked rhetorically, his arms crossing over his chest when he saw Sam grimace, his nose crumpling.

"You’re disgusting," Sam stated, going back to his laptop with a shudder. Dean just broke out into a grin as he pulled out the chair next to him, sitting himself down and leaning back into the seat.

"Nah I’m kidding, I’ve already had my date with Palmela Handerson," he admitted, shaking his right hand and wiggling his fingers, “although some extra lube next time might be nice.” Sam just shook his head, his nose still crinkled as he continued to stare at his laptop.

“I swear our parents dropped you on your head at birth," Sam muttered, trying to ignore his brother’s idiotic grin. Dean just leant forward, lacing his fingers together on the table in front of him.  

“Don’t be so quick judge Sam,” he countered, his grin never faltering. Sam just rolled his eyes, running a hand through his dark locks.

“So, lingerie and sex toys huh?”

“Ohh yeah,” Dean breathed out, his mind going back to the chemise that Y/N had held against her body, the same one he’d fantasised her in. He needed to be careful, he was playing with fire.

“You’re regretting putting no sex in the contract aren’t you?” Sam asked, interrupting Dean’s sordid thoughts. Shaking his head and shrugging his shoulders, the eldest Winchester tried to play off his obvious attraction.  

“Pft no I’m fine,” Dean scoffed, leaning back into his chair before rubbing at his stubble, hoping that his tone was convincing, “totally fine.”


	8. Chapter Six

**Notes for the Chapter:**

> Ahhh guys im sorry! Mind is like a chocolate teapot! I had this update two days ago and forgot to post! 
> 
> Slap me! Haha
> 
> here it is! hope you enjoy
> 
> \- Winchest09

Dean leant back in the leather boardroom chair, one hand resting on his chin the other tapping against the wooden table surface. The current meeting had been underway for well over an hour and all that had been covered was the basic shipments and deals Castiel and Benny had been a part of. Charlie and Kevin were also in attendance to the meeting and he had sent them both a warm smile of appreciation. He was always in awe of how quickly they could hack into security footage, systems and other people’s devices. He was lucky to have such an array of skilled people in his family.

“So the next shipment of weapons is due tomorrow?” Sam asked, looking up from his laptop to Castiel and Benny, waiting for an answer.

“Yes boss, we got a team set up ready to go,” Benny confirmed, his southern twang thick as he answered. Sam nodded as Dean leant forward onto the table, resting on his arms.

“You got a plan to dodge the authorities if they show?” Dean asked, looking up at Cas and Benny from under his brow. Before even of them had chance to answer, the redhead sat at the other end of the table with her own laptop spoke up.

“I’ve already accessed the cameras around the drop off point and created a loop of footage, it’s ready to go, just have to press enter,” she smiled, a little giddy as she relayed her plan. Dean and Sam just smiled back at her warmly.

“Thank you Charlie.” Sam nodded in appreciation. Dean was just about to ask about a contingency plan when Castiel spoke up.  

“…and we will have lookouts placed, we’ll know if something smells off,” he confirmed, which was a reassurance to Dean. This was one of the first big heists they were doing since their failed deal with Crowley, one of the first big heists they’ve done in a while and Dean was desperate for it to go off without a hitch.

“Good,” Dean praised, “now we just need to shift it.” Dean stood up from his seat and began to pace the office, trying to mentally think of all of his contacts. He didn’t want to screw this up.

“Well Crowley used to buy our artillery Dean but he cut us off, remember?” Sam prompted, his face stoic as he looked towards his brother. Dean noticed and he let out a small huff of frustration. Just how long was he going to hold that over him for?

“Get him on the phone,” Dean snapped causing Sam and the rest of the room to jump. Sam pulled out a burner phone, typing in Crowley’s number before handing it over to Dean. He held it to his ear, the dial tone the only sound slicing through the silence before the call was answered.

“Crowley. I have a shipment coming in tomorrow that you won’t want to pass up on,” Dean stated simply, jumping down his throat before Crowley could even mutter a greeting.

“What makes you think I want to deal with you Winchester?” Crowley scoffed.

“’cause you’ll regret it if you don’t.” Dean’s face lacked emotion as he stared blankly at the painting that hung in the boardroom. He knew everyone sitting around the table had eyes on him right now, he had to prove that he was getting this family back on track.   

“Really? What have you possibly got that I would be remotely interested in?” He retorted back, his gruff voice raising slightly at the end.

“Guns. Really big fuckin’ guns.” Dean smirked, the silence on the other end of the line, deafening. He knew Crowley was mulling over his offer, artillery being the one thing he found it hard to say no to.

“Fine, I’m listening,” Crowley said in a short and sharp tone. Dean knew he’d got him hooked, he just needed to reel him in. This was the beginning of his plan, he was starting off small, building up his respect and trust with smaller mobs so he’d gain them as allies.  

“Large calibre guns, heavy weaponry, everything that’s up that little creepy street of yours,” Dean responded, a smirk never leaving his lips. “I can have them ready to go tomorrow afternoon.” Once again only silence could be heard before Crowley took a deep breath, letting it out with a grunt of frustration. That’s when Dean knew he had him right where he wanted him.

“Fine. My house. Tomorrow, 6pm,” Crowley agreed. With that, Dean hung up the phone and threw it onto the boardroom in table in victory, a smug smile riding his lips.

“We’re on,” he confirmed, leaning onto the oak word table. “Once we have the shipment, we’ll transfer it over to Crowley’s Manor,” he explained, looking in Benny’s and Castiel’s direction.

“You’re trading at his manor?!” Sam objected, leaning back in his seat as he used his large hands to gesture towards his brother. “You could be walking into a trap Dean,” he stressed, concern written in his features.

“Sammy I got this alright?” Dean sighed, understanding the worry Sam had for him but he had a plan in his mind, he knew how to manipulate this to get Crowley their on side. “For one, Y/N will be with me.”

“Y/N?” The rest of the room spoke simultaneously. Dean pinched his nose with his finger and thumb, he’d forgotten to brief everyone else on the situation with her. However, he didn’t want them to know the details just yet. With how Sam reacted, he could afford to have them lose faith in him also.

“She’s my secret weapon,” he explained, trying to be as vague as possible whilst still giving an answer. “She’s staying in the guest quarters. If you see her, please be polite and make her feel welcome.” He watched as the rest of the group nodded and Sam went back to typing on his laptop. Just the thought of Y/N made his cock twitch again, the image of her in that black chemise still very, very fresh in his mind. His earlier activity had nowhere near scratched his itch and the only thing that would help was off limits. He wanted to bury himself in pussy, _her pussy_ , but he couldn’t. He had a point to prove after all. “Now if you’ll excuse me, I have some _other_ business to attend to.” With that, Dean hurriedly left the boardroom with his hands in his suit pockets, his fingers brushing against his hardening cock as he walked down the hallway back to his bedroom.  

-

The next morning, Y/N stretched out in her queen sized bed, her arms above her head. She had to admit, she had slept comfortably and for the first time in a long time, she wasn’t waking up every couple of hours to check she was safe. She rolled her head to the side and noted the papers on the bedside table that she placed there when her eyes got tired from reading. Sam had come by early yesterday evening to drop off her research material on the Winchesters, ensuring she would know everything she needed to about the family. She wasted no time and sat herself on the bed to begin work straight away, using her memory exercises to remember key pieces of information and reciting things back to herself to ensure it all stuck in her head.

She was surprised to learn that the Winchesters weren’t as dark as many of the mafia groups she had heard of before, ones that she knew were probably still active. Unlike the others, the Winchesters didn’t deal with human trafficking, prostitution, Class A drugs or worse. They were still into some highly illegal activities but they were ones that didn’t put innocent lives at risk. Shuffling the papers into her hand, she threw off her covers and placed her bare feet into the fluffy carpet. She made her way to her dresser, placing the papers on top before choosing what outfit to wear for today. She looked over her shoulder to see the mahogany table trolley by her bedroom door from the previous night, stainless steel domes littering the surface, covering the whole thing. She smiled slightly, Dean had once again sent her up some food, an array of different dishes for her to try but she stuck with the chicken ceaser salad. Under the bottle of champagne he’d also sent, was a small card which stated he would be taking her shopping today.

It had been a while since Y/N had set foot in a mall or been shopping for that matter. Things were normally bought for her, clothes sent to her room from The Master who wanted Y/N to have a specific look and style. It was rare that clients bought her clothes, that normally only ever happened if they had a specific role play kink they wanted her to uphold. However considering there was no sex in her contract to Dean, she could only assume the shopping trip was for him. _Maybe he wants fashion advice…_

Y/N opened the doors to her wardrobe and pulled out a black off the shoulder shirt dress with a fabric belt round the middle before placing it on the bed. It was the most casual dress she had brought with her. She looked through her underwear drawer and noted that everything she had brought with her was either crotch less, peep hole or push up. Luckily she found a black thong and paired it with the black strapless push up bra she had. She smirked as she held the underwear in her hand, knowing that the way it would make her breasts look would get Dean hot under the collar.

It was two hours later once Y/N had showered, dressed, dried her hair and was just finishing applying her lipstick when a knock sounded upon her door. With one last look in the mirror, she nodded to approve her look, her make up a little heavier than normal but her hair styled in beach waves. She grabbed her purse, slipped on her heels and walked over to her door. When she unlocked it and opened it gently, she was expecting to see her green eyed boss on the other side but instead she was met with a blue eyed man sporting a short beard and a newsboy cap.

“Mornin’ ma’am,” he greeted, a southern accent leaving his lips, “Dean has asked me to escort you to his car,” he continued with a tip of his cap and a smile. Y/N’s confused look softened as she took in the man in front of her. She followed him out and shut the guest room door behind her as she smiled towards the southern man.

“Thank you…” she rolled her words, prompting him to give her a name.

“Benny ma’am, Benny Lafitte,” he replied, his hands in his pockets as he led Y/N down the hallway. With her purse hanging from her shoulder, she held her hands together in front of her as she walked.  

“Well Mr Lafitte, good morning to you too,” she echoed his previous greeting and she heard how he let out a low laugh.  

“Please just call me Benny,” he chuckled, “no need for those formalities with me, ma’am,” he confirmed with a warm smile and it was one that Y/N returned. He seemed warm hearted but she didn’t doubt that he could break some bones if the need arose.

“Noted, Benny,” Y/N replied with a chuckle herself as they descended the stairs to the main hall. Benny rushed on ahead to open the front door for her, allowing her to step through first. Sure enough, at the bottom of the bricked front stairs was the familiar black armoured Range Rover with who she could only assume was Garth in the driver’s seat. As she made her way down the stairs, the back door swung open, revealing Dean who had leant over his seat to ensure she could just slide straight in. He was dressed in a grey suit with a white shirt, his top two buttons undone. She noted how his eyes wandered over her figure as she made herself comfortable in her seat, his green eyes lingering over her chest before moving up to meet her eyes.

“Mornin’ Y/N, sleep well?” he asks politely, a small smile on his lips. She tucked her hair behind her ears as the engine to the Range Rover roared to life.

“I did actually, thank you.” She nodded, her hands automatically going to her lap as the journey began. Dean eyed her for a moment, before nodding himself.

“Good,” he simply replied, resting one arm on his thigh as the other leant on the door. “So I have a meeting we need to attend this evening with an old associate of mine. For that, and for future meetings, you’re gonna need a whole lot of new clothes,” Dean explained, not once looking in her direction, his attention was on the traffic in front of them.

“Wait…this shopping trip is for me?” she almost exclaimed, a crease in her brow. Dean just shook his head, his small smile turning into a smirk as he glanced at her.

“As much as I’d love to take you to a meeting in that delightful little number you showed me yesterday, I’d much prefer to keep those images to myself.” He winked at Y/N with a single wiggle of his eyebrows. Y/N shook her head slightly, to think she thought he was arrogant two days ago. She was starting to think it was just a persona, maybe he was nervous to hire her, from what she had read their family had been through a lot lately so he certainly had a lot on his shoulders. Her mind wandered back to The Master and how he had to approve each item of clothing she wore, if he found out about this…

“…well I have things at my room at The Hemlock you don’t need to-” she tried to control the situation, tried to pull it back into her hands but Dean cut her off, his face like stone as he stared at her.

“-I want you in new things. Things other people haven’t seen you in before.” His response was short, sweet and snappy. How he replied threw her a little, maybe the arrogant thing wasn’t a persona. She couldn’t work him out, granted she hadn’t spent much time with him and she wasn’t going to get to know him intimately but she normally was able to get a reading of the man she was with straight away. She felt like she was look at Dean through fogged up glasses.

“Ok,” was her quiet reply. She wasn’t allowed to argue, wasn’t allowed to put a foot out of place. She knew what was waiting for her when she got back to The Hemlock if she did. Did The Master even know that she wasn’t with her original client? She hoped so, or she was really in for it.

The rest of the drive was silent apart from the low humming of the radio and the few phone calls Dean had made. Y/N didn’t know who they were to but she did assume that they were business related, not that Dean said much in the phone calls to give anything away. Y/N stayed quiet and kept looking out of the window, taking in her surroundings, waiting for Dean to speak to her. It was only when the Range Rover pulled up in a drop off point outside of a very big mall did the elder Winchester decide to speak.

“We’re here,” he said simply before he hopped out of the vehicle. Y/N was about to open her own door when she heard the click of the handle and the summer heat flooded her skin. Garth was standing there with a smile as he held his hand out to help her climb down onto the asphalt.  She thanked him before heading around the back of the vehicle to join Dean in front of the mall. He didn’t say anything to her, just nodded his head towards the front of the mall as he started to walk in that direction. He brought his phone back up to his ear so Y/N could only assume he was still sorting business.

As they entered the mall, she was in awe as she looked around. It was label store after label store, Victoria’s Secret, Armani, Gucci; Y/N hadn’t seen a mall like it before. She followed Dean as he made his way along the marble tiles, a pit of excitement bubbling in her stomach when her eyes landed on each store front. Dean had finished up his call and placed his phone in his pocket, turning to smile softly at her as he stopped outside the front of Ralph Lauren. He motioned with his hand for Y/N to enter the store and with a smile, she did so as he followed behind her.

She didn’t know where to look, her eyes scanning each row of clothes and shoes. It was magnificent, it was everything she thought it would be when she used to look online at the stores. The quiet hustle of customers talking, the tinkering of the piano music bleeding through the speakers along with the polite greetings from the staff. It was something so simple, but to Y/N, it was wonderful. She stood in the middle of the aisle, looking behind to Dean as he caught up with her. However she was confused when he started to look between her and the clothes, a small frown etched in his brow.

“What are you doing?” he whispered, his lips dangerously close to her ear causing her to shiver slightly. She looked up at him with her own little frown, a slight tint flushing her cheeks.

“I’m waiting for you to pick out some clothes,” she stated like it was the most normal thing in the world, her eyes boring into his green ones as he stared down at her. _This is what happens, I don’t have the freedom of choice._ Dean’s face softened before he let out a small chuckle.

“Oh, no. I’m not a personal shopper sweetheart. Go do what you women do,” he encouraged with a wave of his hand which caused Y/N to go wide eyed. _I’ve never picked out my own clothes before._ “Don’t worry about money Y/N, pick whatever your pretty little heart desires.”

“I…” she stuttered, her mind trying to comprehend what was happening, “If that’s what you want.” She started to fiddle with her fingers as she looked around the store, not knowing where to even begin. Her head looking left then right in quick succession as she tried to figure out where to start. _It can’t be that hard, right?_

Y/N was clearly unaware how Dean was watching her. He was used to women taking his cash and running through racks of clothing, having arms full of designer gear before he could even sit down. But this was different, he crossed his arms over his chest as he studied her body language. The way her fingers tentatively touched the fabric of a shirt, how she was looking around the store. He took a deep breath, letting the frown in his brow deepen as he continued to look in Y/N’s direction, allowing a mutter of his thoughts to pass his lips.

“She’s acting like she’s never picked out clothes before.”


	9. Chapter Seven

**Notes for the Chapter:**

> Apologies this took longer than normal but it's here, i hope you enjoy!
> 
> \- Winchest09 x

Dean continued to watch Y/N for a few more minutes, observing her movements and judging her body language. She wasn’t snatching things off the rails to try on, in actual fact, it had been ten minutes and yet she was still to pick out a single item of clothing. He unfolded his arms from his chest and placed one in his pocket to retrieve his phone. He needed to know more about Y/N, where she had come from, what her life was before. She was niggling at his curiosity. After unlocking his phone, he scrolled through his contacts and dialled the only person he knew would be able to help him in this instance.

“Hey Charlie, I need you to do some digital digging,” he commanded immediately after Charlie answered the call.

“Well good morning to you too,” she huffed sarcastically before yawning, “but sure, no problem, what do you need?” she asked eagerly as Dean heard the sounds of her laptop starting up.

“Go to Sam and ask him for the folder on Y/N. I need you to do some digging for me, see what you can find out about her, where she came from, where she was born and so on and so forth,” he muttered as he continued to stare in Y/N’s direction, making sure she didn’t have any chance of overhearing his conversation.  

“…ok,” Charlie replied, her tone not hiding her confusion. Dean let out a slow breath, he knew it was only yesterday he had been vague with his team about Y/N and now he’s asking one of them to go snooping through her business.

“Everything that we know of her is in the folder. But Charlie?” he questioned, “this is to stay between you and me, alright? Whatever you find, you come straight to me. Do not talk to anyone about this, do not show anyone her file, am I clear?” he asked in an authoritative tone, his eyes not leaving Y/N as he did so.

“Crystal sir,” she replied, “I’ll get back to you as soon as I can.”  

“Thanks,” Dean smiled a small smile before ending the call. He was hoping that Charlie would have something for him within a few hours. Placing the phone back in his pocket and taking a deep breath, he started to walk over to Y/N whose arms were still bare of clothes.

“You alright here Y/N?” he asks calmly, bending down close to her ear. The sudden intrusion of words caused her to jump slightly, clearly bringing her from whatever daze she was in.

“Huh? Oh yeah.” She sent a soft smile his way as she continued to finger the clothes on the railings. “Just so much to choose from,” she explained with a slight shrug of her shoulders, pushing each hanger to the side. Dean frowned slightly as he rubbed at his stubble.

“Online more your thing, eh, sweetheart?” he insinuated, a little smirk on his lips. He was trying to find reason in her behaviour, maybe she was an online shopper and just didn’t like to be around that many people. It was a valid reason but it didn’t sit right with him, especially when she was in such a _people pleasing_ occupation.

“What?” she asked, her head turning slightly towards Dean, a crease in her brow, “oh, shopping online. Yeah, less people, no queues,” she reasoned as she moved across the aisle to the section of dresses. Dean stood in place and watched her as she moved. He didn’t quite know if he believed her or not; he was sceptical to say the least.  

“Uh huh,” he replied casually as he continued to follow Y/N around the store, watching her hands as she fondled random pieces of clothing.

“Plus it’s easier to choose when it’s your own money you’re spending. I don’t want to overstep my limit here, Dean,” she replied politely, stopping looking through the rails to look up at him from under her long lashes. Dean felt his resolve break a little as she stared up at him, maybe she was _just_ being polite. Maybe there wasn’t an underlying reason as to why she wasn’t carrying as many clothes as her arms could hold.  

“There’s no limit Y/N,” he said softly, smiling down at her as his hand came to rub the tops of her arms gently. “Tell me, has anything caught your eye?” he asked, dropping his hands to his sides as he tried to encourage her to shop.

Y/N nodded a little, her hands rubbing at the tops of her arms as she walked back to the rail with a few dresses on them. She pointed out to a black knee length dress, singling out her size and picking it up to show Dean. He hummed in approval, his lips pouting slightly as he nodded. She then moved over to another rail and picked up a belted knee length polka dot dress and Dean bit his lip slightly, he couldn’t wait to see her in them. With another approving nod, Y/N hooked the hanger over her wrist and continued to move around the store but she kept looking over her shoulder to ensure that Dean was still close to her. In fact, he was looking through the railings himself. Not that he wanted to control what she was going to wear, not at all. He had just simply noticed a few outfits that he would love to see her in, outfits that he knew would complement her figure wonderfully.

“Would you mind if I offer some recommendations sweetheart?” he asked as he held a gown in her size behind his back.

“No, not at all.” Dean noticed how her eyes were brighter than they were a few minutes ago, her body language had changed slightly and it made him happy to know her guard was coming down a little. With a slight smirk, Dean pulled the dark floor length from behind his back and held it close to his chest.  

“I think you’d look downright fuckable in this,” he confessed which earned him a few snooty looks from the staff members in the store. Y/N noticed and stifled a laugh at their reactions before she ran her fingers through the fabric. The dress material was soft to touch. It was beautiful, simple, and elegant with a slit up to mid-thigh on one side. Dean knew he’d chosen well by the look on her face.

“…fuckable?” she repeated, an arch in her brow but a playful look on her face, “You really do have a way with words Dean, makes me feel all tingly inside,” she teased, a smile wide on her lips as she gently took the dress from his hands. Dean tucked his hands in his pockets as he felt his cock twitch at her words, his mind flashing back to his pornographic fantasy with her from yesterday.  

“I can make you feel more than just tingly, doll,” he retorted, his voice a low rumble as he rolled his bottom lip into his mouth with his tongue. His emerald eyes held her gaze for a moment, her pupils dilating slightly before she looked away.

“We’ll see, Winchester,” was her simple response as she walked towards the changing room, a few more garments on her arms.  

Dean just watched her go, a confident sway in her hips and he rubbed at his chin. Why did he have to put no sex in the contract? If he could go back in time, he’d slap past Dean over the head and tell him not to be so stupid. Sure he had a point to prove with his brother but sleeping with the same on women over and over wouldn’t have been as harmful as his one night stands. He grumbled under his breath as he looked up towards the ceiling, he knew today was only going to get worse. He was taking her underwear shopping next, she needed normal panties and bras, considering most of hers were peepshow or crotchless. He was his own worst enemy.

Half an hour had passed and he was walking out of Ralph Lauren with a more relaxed Y/N next to him. He hadn’t told her where they were heading next but when they rounded the marbled corner, her eyes widened slightly as they walked towards the entrance.

“Victoria’s Secret?” she asked, looking up at Dean.

“It’s my favourite store in the whole wide mall,” he grinned as he winked down at her.  

“I’m sure it is,” Y/N retorted playfully. Dean chuckled as they entered the store, his large hand coming to graze the bottom of her back as he leant down to her ear.

“As much as I love those crotchless little numbers and peephole bras, I thought you’d like something a little less breezy for our meetings,” he whispered, a low rumble coming from his chest as his eyes connected with hers. With his one bag free hand, he gestured throughout the whole store. “Go nuts.”

Y/N just shook her head gently at him, a soft smile playing on her lips. Dean noticed she was becoming more comfortable shopping with him. She immediately took to the rails, her eyes lighting up like a kid on Christmas morning. Something was still not sitting right with him about it all. Even if she does enjoy online shopping, why would she seem so excited to have this freedom of choice? He pulled his phone out of his pocket and checked for messages off Charlie but there was nothing. He only hoped that she would find something that would explain this to him.

“Are you coming?” Y/N asked causing Dean to look up from his screen to see that she had already got a handful of garments slung over her arm. He frowned slightly at her question, sliding his phone back into his pocket as his eyes switched from the underwear to her.

“W-where?” he choked on his words, covering his stutter with a cough. The idea of seeing her getting changed into underwear caused his cock to harden slightly, but he tried to play it smooth so he didn’t seem too eager to see her in barely nothing.

“I need to try these on, sometimes the sizes in here can be little funny,” she stated as she looked at the tags of the garments, not paying any mind to Dean’s stutter. She looked up at him through her thick lashes, twirling the labels in her hand as she coyly bit the corner of her bottom lip, “plus I don’t really want to go alone.” She swayed slightly on the spot as she awaited Dean’s answer and he had to wonder whether she knew what she was doing to him.

“Lead the way, sweetheart,” he said as smoothly as possible, one hand gesturing for her to show him the way to go. Her lips broke out into a beaming smile as she walked past him quickly, her heels clicking against the floor. He followed on, taking a deep breath as he did so. He was playing with fire and he knew it.

As Y/N led them into the changing room, she chose a stall and pulled across the plush curtains to block the view. Dean sat down on the plush faux fur covered stool outside of her changing room. His hands clasped together as he leant forward on his knees, rubbing his thumbs together. He heard the sound of Y/N’s dress unzipping and he was doing all he could to not let the images run through his mind but it was useless. His focus landed on the gap between the floor and the curtain, a pair of lace _crotchless_ panties fell around Y/N’s ankles before he caught sight of her hand pulling them over her heels. He inaudibly groaned, all this time she’d been in his company, she’d been wearing crotchless underwear. His cock twitched in his suit trousers and Dean sat up straight, looking each way before using his hand to rearrange himself.

Just as he pulled his hands out of his trousers, the sound of the curtain being pulled back caught his attention. Dean’s eyes went a little wide when he saw Y/N standing there, wearing some sort of floral embroidered bra with lace that stopped above her waist. It was paired with a matching lace thong. His eyes went a little wide as he took her all in as she twisted and turned in front of the mirror. Sure he’d seen her in her underwear in photos but in real life? It was something else.

“What do you think?” she asks coyly, her eyes trained on his through the mirror. Dean swallowed thickly, he didn’t know how to respond without sounding like a sex depraved teenager.

“Y-yeah, they look good,” was his strained response as his eyes began to take in all of the lace detailing of the bra, the way the cups were moving with each breath Y/N took.

“Good?” she questioned as she turned to face the mirror fully, eyeing Dean in the reflection. He watched how her fingers traced over her skin slowly, how they skimmed past the straps to the edging of the lace on the bra itself, skimming her breasts. “Hmm, so is this exactly what you want?” she teased.

“Sweetheart, you have what you want and what you’re comfortable in.” Dean tried to control the situation, to not give in to his now throbbing erection that was pressing against its confines. He had to stay leaning forward, he couldn’t allow Y/N to know what she was doing to him. She smiled softly at his response, her hands trailing down towards the material of the thong she was wearing.

“I will but with you being my client and all…” she let her sentence trail of as she turned back around to face Dean fully, her fingers hooking under the lace of her panties as she adjusted them a bit more, “just wanted to make sure you’d be happy with your purchase.” The look she was currently sending towards Dean caused him to feel winded, he was sure his dilated pupils were giving away just how much he wanted to slam her into that changing mirror and fuck her senseless. He’d ruin those panties before he’d even bought them. He wanted her lips to be swollen from his kisses, her skin to be red from the scratch of his stubble. He wanted his cock to be buried deep within her dripping pussy.

“Oh, I’m happy sweetheart,” he answered breathlessly, looking her up and down, his tongue running along his bottom lip as he drank her in. With a simple nod, she turned on her heel and slowly closed the curtain, keeping eye contact with him through the mirror till the last possible second.

Once the curtain was closed, Dean let out a long breath and leant back against the wall, palming his throbbing cock through his trousers. He needed release, he needed to get back to his bedroom and stay there until he’d calmed down but he had a long way to go before that could happen. Y/N had a few more pieces to try on before they moved on to shoes and any other personal items she may need. With a groan, Dean ran a large hand down his face. He was like a sinking ship when it came to her, and he was going down, fast.

*

Shopping bags in one hand, his other in his pocket next to his calming erection, Dean lead Y/N into one of his favourite little bistros within the mall. He pushed open the door, a little bell chiming above them signalling their entry as he held it open for Y/N to walk through first. He noticed how she was looking around and he hoped that she would appreciate it as much as he did. It was quaint, soft redwood walls paired with French Parisian furniture helped contribute to the warm welcoming atmosphere. Hanging baskets filled with ferns hung from the walls in between stained glass lamps, and the air smelt of fresh pastries. It was heaven.

Dean led Y/N to his usual table in the corner and pulled out a chair for her, waiting for her to take her seat. Once he sat opposite her, he rearranged his suit jacket to be comfortable as Y/N picked up a menu from the middle of the table.

“You need to try the pie, it’s amazing,” Dean gushed as he signalled for the waiter to come over to them.

“Thank you but I’ll just have a sparkling water,” she replied politely, folding her menu and placing it back on the table. Dean frowned as she placed her hands in her lap and he leant forward slightly, placing his hands on the table.  

“You not hungry sweetheart?” he asked softly as the waiter approached the table, a pad in hand ready to take the order.

“Not particularly,” she responded with a shrug of her shoulders.

“If you’re sure,” Dean continued and she just nodded for him to go ahead and order to which he did.

Not long after, their order arrived at the table. A fairly big slice of pecan pie, paired with a beer for Dean and a sparkling water with a lemon for Y/N. He couldn’t wait to dig in, his stomach rumbled as soon as the pie was placed in front of him. Fork at the ready, he dug into his treat and the groan that left his mouth was near enough orgasmic when he tasted it. He looked up to see Y/N smirking into her water.

“You want me to give you and the pecan pie some privacy?” she teased but Dean paid no mind to it. Instead he just cut another piece with the side of the metal utensil.

“It’s so good. Here,” he offered, holding the pie covered fork in front of Y/N however she pushed her head back, frowning slightly.

“No really, I’m ok.” She looked away from him and the piece of pie was offering her and Dean frowned harder, not understanding her reaction.

“It’s a bite,” he tried to reason but she just shrugged again, pushing the fork back towards him.

“I’m fine honestly, I don’t eat much.” She held Dean’s gaze for a second, his eyes flickering from one to the other as he tried to work her out. He’d noticed already the choices of food she made, the healthy dinners and breakfasts so he let it slide, thinking his was just another healthy venture.

“Noted,” was his simple response as he shoved the piece of pie into his mouth and continued to devour the rest that was on his plate, stopping to sip his beer every now and again. He was sharing a comfortable silence with Y/N. He kept glancing at her, watching her people watch, her finger slowly circling the rim of her glass.

“So, I went over the files Sam brought to my room last night,” she mentioned softly, breaking the silence between the pair. Dean stopped eating and looked up at her, fork still in hand, his eyebrows raise.

“And?” he prompted and Y/N just sighed as she leant forward onto the table.

“Without me stepping out of line Dean, I mean no disrespect, but what happened?” she asked, her fingers playing with each other.

“What do you mean?” Dean wiped his mouth with a napkin after eating the remainder of his pie.

“You guys, The Winchesters, were the top dogs around these parts. You ran most drug and weapon trafficking organisations, you dealt with luxury car trafficking and money laundering. You were feared, respected,” she explained as Dean looked at her intently, “I guess I’m curious to see how the empire fell so fast.”

“The empire as not _fallen_ sweetheart,” he somewhat snapped, throwing the napkin down onto the table next to him, “I don’t need to go into details Y/N, you know about the assassination of my parents,” he growled as he picked up his beer and he saw how she leant back away from his slightly.

“Of course but what I don’t understand is how things ended up this way,” she confessed and he tensed.

He didn’t want to reveal the truth to her, not yet. It was hard for him to accept it himself. He knew he’d fucked up, his brother reminded him of that daily. Yes he buried his head in the sand but he felt like it was justified considering the circumstances. His jaw clenched and his grip on his beer bottle became tighter.  

“Look, losing your parents the way I did, it fucks you up alright?  Sure, we got burned but we’re just biding our time before we rise from the ashes,” he stated, his expression stony as he looked into Y/N’s eyes. He knew he shouldn’t go on the defensive but it appeared to be his default setting. Y/N retreated into herself a little, picking her drink up to take a sip from it once again. A phone ringing broke the uncomfortable silence between them. Dean reached into his pocket and pulled out his phone. Seeing Charlie’s name flash across the caller I.D made him stand immediately.

“Excuse me, I need to take this.” He dismissed himself from Y/N’s company and stormed his way outside of the bistro, answering the call as he did so. “Charlie? You got anything for me?”

“She’s an escort Dean, really?!” Charlie chided down the phone at him, a little scoff at the end of her sentence. Dean rolled his eyes, he knew she would find out this information so he was already expecting the ear bashing that was on its way.

“Can we…let’s move past that and focus on what I asked you,” he commanded, a hand going into his trouser pocked as he glanced over his shoulder at Y/N who was still sitting in the corner. He heard Charlie let out a loud and long sigh, her fingers tapping at a keyboard.  

“Well, she was born in New York, went to school then college. Majored in language studies, straight A student all the way through. No serious medical illnesses, no broken bones, no felonies; looks like you got yourself an _angel_ there, Dean,” she explained, a little sarcasm in her tone.

“That’s it?” Dean prompted after a few seconds of silence, a frown on his brow.

“Why? What were you expecting?” Charlie fired back, her fingers still tapping away at her keyboard.

“I-I don’t know. Just, something.” Dean rubbed at his forehead as he paced back and forth outside the bistro. “Just, keep on it for me. If anything odd pops up, I need you to tell me straight away,” he ordered in an authoritative manner.  

“Sure thing,” Charlie complied and he ended the call.

Sliding the phone back into his pocket he turned to look at Y/N again through the bistro window. Something wasn’t adding up with her, she was _too_ clean for someone who is now working as a high end escort. If she was a straight A student, she could have any career she set her heart on. She had the brains, she definitely had the beauty and from what Dean had already seen, she had some fire in her belly. Dean knew there was more to her story, he just had to figure out what it was.


	10. Chapter 10

**Notes for the Chapter:**

> Guys!
> 
> I'm so sorry I have taken so long to update this fiction! I recently returned to work after being off on maternity leave and it messed me up no end ha! I was worn out and it took me a little while to get into a routine and feel like me again! 
> 
> Anyway!
> 
> Here's the new chapter! I hope you love it!
> 
> Thanks for your patience. 
> 
> -Winchest09

Y/N looked into the dressing table mirror at her reflection, rubbing her lips together to spread the red lipstick she had just applied. She was due to leave with Dean shortly to attend the meeting with Crowley and she wanted to look her best. On the way back from the shopping trip, Dean had told her what was expected of her this evening, that displays of affection would be needed from the moment she left this room until the moment she arrived back to the manor later after the meeting. When Y/N had asked him how he would like her to dress, Dean just shrugged his shoulders and told her that it was up to her. He wanted smart but sexy but gave her the freedom of choice. A small smile graced her lips when she looked back at herself in the mirror, she could only hope he would approve of her look. She’d chosen to go with the short knee length backless black dress with heels, she’d left her hair loose and natural and created the smoky eye look with the make-up she had.

“You ready to go, sweetheart?” Dean’s voiced sounded through the door after two small knocks. Y/N grabbed her purse and quickly headed over to her bedroom door. As she opened it, she was met with Dean’s stunned expression, his eyes looking her up and down as she stood there.

“Is this alright?” she questioned, a little concerned that this wasn’t the look he wanted.

“Y-yeah, you look good Y/N,” he stuttered as his green eyes roamed up her figure to meet her own but she frowned slightly. _Good._ She had started to second guess herself, she had begun to think that she had made the wrong choice and that he was going to be mad with her.

“Good? I can change just give me 5 min-”

“No. You look amazing, just what I had in mind,” he complimented, reassuring her that she didn’t have to worry. Y/N just nodded, her small smile returning as she stepped into the hallway, closing her bedroom door behind her.

“Ok then. Let’s go get you this deal.” She automatically laced her arm through his as they walked side by side through the corridor. She did initially think about holding his hand but when she noticed that Dean’s hands were firmly in the pockets of his suit trousers, she knew that linking her arm in his would be the appropriate way to go.

As they walked to the car, Y/N couldn’t help but be enveloped by Dean’s aftershave, a man that smells nice was always a bonus and Dean smelled _incredible._ His crisp black suit made him look incredible as well, his top few shirt buttons undone for the more casual look, a style that certainly suited him. As he reached forward for the manors front doors, Y/N felt how he removed his hands from his pockets and placed on large palm on the bottom of her back, his fingers just lightly gracing her skin. Tilting her head to look up at him, Dean flashed her a quick smile as he encouraged her to the car.

As always, Garth was waiting by the back doors and opened them up as they grew closer. She sent a warm smile his way in thanks before she slid onto the plush leather seating. She buckled herself in, smoothing down her dress to avoid creases before turning her attention back to the green eyed man next to her, the cars low rumbling engine her base track for her conversation.

“So I took the liberty of doing some digging on Crowley last night,” she casually stated, pulling her compact mirror out of her purse to check her lipstick. Dean just turned his head slightly to look at her.

“Is that so?” he questioned, a slight smirk resting on his lips. She hoped he was happy with what she had done, the last thing she wanted was to step out of line.

“Figured I needed to know as much as I could to help you out with this deal,” she spoke softly, shrugging as she clicked her compact mirror closed and placed it back into her bag. Suddenly, she became very aware of a sudden warmth radiating through the thin material of her dress onto her leg. Glancing down, Dean’s hand was resting upon her thigh, giving her a leg a slight squeeze.

“Sweetheart, as great as that is, sometimes you need to just go with the flow. Crowley can be manipulative, two faced and a pain in the ass,” he explained, all the while his hand was still resting on her leg.  

“It’s nothing I can’t handle,” Y/N reinforced, placing her smaller hand on top of his. She caught his gaze briefly and she noticed the slight apprehension in his eyes.

“I hope you’re right,” he said lowly, giving her leg on last gentle squeeze before removing his hand completely and looking out the window. As they drove through the dark towards Crowley’s manor, her mind wandered. With all of her clients, Y/N had always performed to the specification given to her as that was her job whether she liked it or not. In this instance, she was eager to please Dean so she wanted to do whatever it took to ensure that he would get the deal he was looking for.

Y/N felt the car slow down as it turned a corner, two large gates at the end of a dirt path which she could only assume was the entrance to the manor. They waited a few moments before the gates opened, the car slowing down on its approach to the front entrance. Just like the first time she saw where Dean resided, she was in awe. The manor was huge but dark, gargoyles resting on stone balconies, large statues of medieval type warriors and demons lined the steps to the front doors. She took a large breath, steadying her own nerves as Garth exited the vehicle to come and open her door. This was it, show time.

Immediately upon exiting the car, Y/N walked around to Dean’s side, her head held high as she faced what she could only assume were Crowley’s henchmen at the top of the stairs. She was about to lace her arm with his once more when Dean’s arm snaked around her waist to pull her closer, his lips pressing gently on her temple. She smiled a natural smile, there was nothing forced about her reaction even though she knew he was only acting for the benefit of this meeting. Climbing the stone stairs, Dean nodded towards the henchmen as they opened the door to the manor.

As Y/N walked in, she looked around to study the grand hall. It was dark, the room a mixture between red brick and black wallpaper. The windows where draped in red curtains and veils, the flooring was a mixture of dark oak wood with red long rugs to accentuate the room. She felt Dean’s hand tighten slightly on her hip and when she looked at him to see him staring in a certain direction, she guessed why. A member of Crowley’s crew had come into the hall and with a flick of his wrist, had gestured for them to follow him. Taking a deep breath, she walked with Dean, his hand still tight on her waist as they followed the man wherever he was taking them. When they reached some darkened double doors, the henchmen opened one of them and held it open, an invitation for them to enter. Dean let go of her waist but encouraged her to step behind him. Whether it was a subconscious move to try and keep her safe she was unsure, but she appreciated the sentiment.

The room they were entering matched the décor of the rest of the manor, dark and brooding. Stone walls, red velvet curtains and rugs. There were a few high backed armchairs resting by an open fireplace, a drinks cabinet next to it filled with an array of bottles and a few bookcases with literature dotted around the room. Her eyes landed on the figure that was standing in front of the fireplace, his hands behind his back as he turned to face Dean. His hair was dark, receding slightly at the front but his short beard accentuated his features. She could only assume that this was Crowley.

“Dean, Dean, come in. Please take a seat,” his rough voice sounded, gesturing his hand to one of the high backed chairs. Suddenly, his dark eyes moved from Dean to Y/N, his eyebrows raising slightly as he approached her, “and who may I ask is this enchantress you’ve brought with you?” he drawled, a hand on his chest before he took her hand in his free one, bending down to kiss it gently. Y/N just smiled politely as he stood, gently pulling her over to the free chair by the fire as Dean took his place in the one next to it.

“Crowley. This is Y/N,” Dean introduced, “ _My_ better half,” he continued, accentuated the words to he would communicate to Crowley just who she belonged too. Y/N sat in her chair, crossing her legs and placing her hands in her lap as she watched the scene in front of her unfold. Crowley just raised his eyebrows at Dean as he sat himself in his chair.  

“Better half? So you’re telling me you’ve finished sowing your many wild oats? I find that hard to believe,” Crowley scoffed, reaching next to him for his glass of Scotch. Y/N noticed how Dean stiffened slightly, his smile slightly forced as he leant back in his chair, his fingers rubbing together.  

“What can I say, she has a way with me,” came Dean’s response to which Crowley laughed.  

“Seriously? She’s honestly with you?” he questioned again, taking a sip from his glass. As she sat there, watching, she began to process Crowley’s mannerisms, the way he held himself and the way he talked at Dean. It was clear that the respect Dean wanted wasn’t there, something that she knew he had hired him for. She had to play this just right.

“What do you want? Proof?” Dean remarked, a slight scoff in his voice as he stared Crowley down but he just smirked in response, shrugging his shoulders slightly as he took another sip of his drink. It was a silent challenge to Dean and she knew it. _This was her chance._ “C’mere, sweetheart.” Dean beckoned with one finger, his green eyes glancing over at her as she stood slowly, “on your knees,” he continued as she stalked in front of him as he undid his belt.

“Please, how many whores have sucked your cock?” Crowley scoffed, clearly unimpressed with the show. _She had to up her game._

“He’s right,” she agreed as she slowly leant forward over him, batting his hands away as she continued to open his fly, her eyes never leaving his as she did so. She watched how his pupils dilated and how he took a deep breath as she yanked on his trousers to ensure the fly was wide open. She slowly slid her small hand across his thigh, finding his hardened cock underneath his boxers and she grinned. She leant forward a little more, her red painted lips ghosting past his ear, “it’s much more fun when you’re on _your_ knees, sweetheart,” she teased, her hand squeezing slightly at the bulge in his boxers. She heard him swallow hard and when she pulled back to look at his face, his lips were parted. 

“Baby, you know if I go down there, I won’t want to get back up,” he retorted, a cheeky smirk on his lips. With a raise of one eyebrow, she lowered her body on his and placed a searing kiss on his lips. His hands immediately found her sides, his fingertips bruising her skin as she massaged her lips with his. Her one hand still rubbing at his now twitching cock as the other kept her balance. She felt her own arousal pool between her thighs, even though Crowley was there watching, even though this was just for show purposes, she could deny the obvious attraction she had to Dean. With a slight sigh, she withdrew from his lips, capturing his bottom lip between her teeth as she did so.

“Looks like I know where you’re going to be spending your evening then,” came her response as she used her manicured fingers to rub the lipstick from his lips. Dean didn’t reply to her, he only kept his grip tight on her sides as she tried to stand, encouraging her to sit in his lap. Y/N made herself more comfortable and snuggled into the Winchester, placing an arm around his shoulders as she did so. His cock was still digging into her upper thigh, a constant reminder of his attraction towards her. Something she wished she could make use of. In this instance, she really wished Dean wasn’t that much of a gentlemen and had kept sex in their contract.  

“Well, I would ask how much you’re paying her, but I have to admit, your chemistry is undeniable. You’ve finally found someone whose balls are as big as yours, Winchester,” Crowley’s voice sounded in the room, causing both Dean and Y/N to look his way. “She’s feisty, I like her,” he confirmed and Y/N smiled. _She played it right._

“So, let’s talk business,” Dean husked, one large hand rubbing at the small of Y/N’s back and the other on her bare legs as he stared Crowley down.  

“This shipment you have, what makes it worth my time?” Crowley questioned, swirling his scotch around his glass. She heard Dean take a deep breath.

“You know what kind of weapons they are Crowley, military grade; that is what makes it worth your time,” Dean replied, his voice gruff.  

“Hm,” Crowley responded, clearly unimpressed. Y/N felt how Dean was quickly getting frustrated, his once hard cock that was digging into her thigh had softened yet the grip on her become a little rougher. _Time to shine._

“If I may, Dean,” Y/N asked softly as she turned to look down at the green eyed Winchester, he looked up at her and studied her eyes for a second, wondering if he could trust her. The soft smile she gave him encouraged Dean to nod, allowing her to continue. Taking a deep breath, Y/N turned to face the dark haired man, her hands crossing in her lap as she sat a little more straight. “Crowley, from what I know about your mob is that you deal highly with paid assassinations. Whether that be on a singular scale or whether it’s genocide, it’s your forte is it not?”

“I do like to take a few lambs to the slaughter,” Crowley confirmed, his eyes never leaving Y/N. She felt Dean’s hand on her back move slightly, rubbing his thumb back and forth in encouragement.  

“So, you do understand how beneficial this shipment of weapons would be to you. Just think of your profit margin,” she explained, staring into the eyes of Crowley. She watched how he sat forward in his chair, rubbing his fingers over the edge of his glass before scratching at the beard on his chin.  

“You make a good point, darling, I’m just unsure if I could trust your _sweetheart_ over there,” he explained with some malice in his voice. _This just won’t do._ Y/N knew of what had gone down between them, she had read that in her research so now, she had to help repair the damage.

“Fergus, I can call your Fergus right?” she asked as she left Dean’s lap, walking to stand in front of the fireplace as Crowley nodded, “I can tell that you’re a man that likes his luxuries, the 30 year old Craig scotch in your hand says it all, not to mention the Armani suit. With this shipment, you’re business will grow tenfold, earning you many more luxuries in the future. In regards to Dean, he brought the shipment here, no strings, no elaborate plan to pull the wool over your eyes, no authorities on our tail. We’re wanting to get the business back on track, a track which starts with your cunning self. I can also help to ensure that these things run smoothly and there is nothing I’d love more, than for things to run _smoothly_ between us.”

As she was in the middle of her speech, her fingers found the neck of the scotch bottle and had topped up Crowley’s glass as she slightly flirted with him. There was a long pause of silence as she placed the bottle back down on the side, no words being said. She turned to see Dean and Crowley staring each other down before Crowley’s eyes landed back on her. She looked towards Dean discreetly and noticed how he, too, was staring at her now. She smiled and walked over to him as he held his hand out to her, pulling her back into his lap and placing a soft kiss to her shoulder. It was a silent confirmation that he was happy with what she’d done. 

“And I’m guessing you want my money and loyalty in exchange for regular shipments?” Crowley asked, taking another sip from his freshly refilled glass.

“Same as always,” Dean confirmed, a slight smile on his lips as Crowley nodded. He placed the glass on the side before wiping his hands on the handkerchief he pulled from his pocket. He sent Y/N a smile and wink as he leant forward, offering an outstretched hand towards Dean.

“Then you’ve got yourself a deal.”

-

It was a little after midnight by the time Y/N and Dean had arrived back at the Winchester Manor. After confirming a deal, Dean and Crowley ironed out their differences over a glass of scotch and talked more about the shipments that would be coming in the future. Crowley had also inspected the weapons and gave his compliments to Dean, he was clearly impressed. Dean left happy, his hand never leaving Y/N’s body the whole way home. She knew it was still for show, even though they were only in the presence of Garth, it was still something he continued with. When they got back to their own abode, Dean was quick to get the door for Y/N instead of Garth and dismissed him for the night. His hand snaking around her waist once again as he guided her up the front steps and through the front door.

Dean made it clear that he wanted to celebrate this win with her, telling her to go and wait in the living room whilst he went to grab his favourite bottle of whiskey and a couple of glasses. Y/N agreed, enjoying being in his company, so she made her way to the couch and made herself comfortable at the end. She pulled off her heels and tucked her feet under her, running a hand through her hair as she waited. It wasn’t long before Dean was sitting at the other end of the couch, filling her glass and making a toast to business.

“Sweetheart, you were amazing today,” he complimented as he leant back into the couch. He had discarded of his suit jacket somewhere between entering the kitchen and joining her in the living room. He looked a lot more relaxed than he did earlier on in the evening, it was a nice sight to see.

“Thank you, all in a day’s work,” she replied, staring down at her drink as she ran her finger around the edge of the glass. There was a moment of silence that fell between the pair but it wasn’t uncomfortable by any means. It was nice to be in the company of a man that wasn’t demanding her attention all the time that allowed her to relax and take a breather. She couldn’t remember the last time she felt this comfortable.   

“Speaking of work,” Dean mentioned, breaking the silence as he took another sip of his drink, “if you don’t mind me asking, how long have you been in the escort business for?”

Of course. She was wondering how long it would be until this question appeared. All of her clients had, at some point, asked her this question. Sometimes it came after a sexual act and they had branded her _the best they’d ever had._ Sometimes it came at the beginning of a relationship as the client wanted to know just _how_ experienced she was and then sometimes, just like now, it appeared after a job well done.

Let’s just say a long time,” she said softly, her hand still in her hair as she answered. It was the answer she had been trained to say. She knew she wasn’t allowed to say she’d been working at The Hemlock since she was six years old as that would expose everything her master had worked hard on.

“Have you never thought about doing something else with your life?” Dean asked softly as he looked over at her, a sincere smile on his face. Y/N took a deep breath, this was a question she’d never been asked, it threw her slightly off guard. _Remember your training._

“Sometimes but then I’m extremely good at what I do and I make some good money.” She shrugged. _You liar._ “I get to travel and see the world.” She forced a smile, trying to see the good in what she does. In truth, she had thought about what her life would be if it was her own, she’d scribbled those thoughts down in a journal that got found by one of her master’s henchmen. An action that had her beaten and put into isolation for a week. She learned to never dream again.

“Do you ever get a break, like a holiday to do your own thing?” Dean asked another question that threw her.

“Every day’s a holiday Dean,” she chuckled slightly, trying to throw him off her scent, “enough about me though. We’re meant to be celebrating your win.” She raised her glass to his and let them clink slightly as she shuffled closer to him on the couch. She needed to distract him from the conversation about her.

“Our win sweetheart,” Dean corrected, moving his arm so it rested along the back of the couch behind her, “you were amazing with Crowley. That little display of yours too, pretty sure he got hard from it,” he joked, finishing the rest of his drink before leaning forward and placing the empty tumbler on the coffee table. Y/N smirked slightly into her own glass, remembering the feeling of his _generous_ erection under her palm.

“So did somebody else,” she retorted, her eyes glistening with mischief as she looked into Dean’s green orbs. Dean leant back and undid a few more of his shirt buttons with one hand, a small smile on his lips as he did so.

“You were fucking hot, take it as a compliment,” he said nonchalantly, as if it was no big deal that he got hard under her touch. “Tell me, did the feel of my hard cock make you wet, baby?” he teased, his hand tickling the back of her neck. She hoped he didn’t see, but the way his fingers brushed over her neck made goose bumps arise on her skin.

“It takes more than a hard cock and a heated kiss to get me going, Dean,” she purred, sliding her free hand over his thigh in the same fashion she had done earlier that day, her fingers teasingly close to his crotch.

“Oh really? Care to share with the class?” Dean questioned, his green eyes roaming over her figure as he did so. She knew what was running through his mind, if he could, she was sure he’d be undressing her here and now.

“It’s something you’d have to figure out on your own,” she teased as she removed her hand, “Oh, wait. You can’t. Shame about that no sex deal huh?” She smiled a coy smile as she finished the rest of her drink.

“I don’t need sex to figure out what would make your pussy drip for me, sweetheart,” Dean husked, his fingers sliding along the nape of her neck. She didn’t show it but the way those words bled from his lips made her sex throb.

“Is that so?” she retorted, one eyebrow raised as she placed her glass on the table to join Dean’s. When she straightened up, Dean was closer to her side, his fingers sliding down the top of her arm.

 “I’m going to have you eating out of the palm of my hand,” he said lowly as he pulled his bottom lip through his teeth. His aftershave washed over her once again and she had to squeeze her thighs together. Sure, the no sex thing was a gentlemanly act, one that she was appreciative of but due to the nature of her job, it meant that Y/N also had a high sex drive. She leaned forward into him, her lips inches away from Dean’s once again.

“…and I’m gonna have you on your knees, begging for me,” she breathed, her Y/E/C eyes looking deeply into his green ones as he held her stare.

“You wanna bet?” he goaded, his lips curling up one side into a playful smirk.

“Oh, I know,” she responded as she ghosted her lips over his, her nose nudging at Dean’s as she teased him. She felt how he leaned in and chose that moment to move away and stand up, making her way to her bedroom to retire for the evening, “good night, Dean,” she called over her shoulders as she swayed her hips in a tantalising manner. As she turned the corner, she heard his gruff voice call after her, a playful tone lacing his words.  

“I’ll make you break your contract, Y/N. Just you wait and see.”


	11. Chapter Nine

**Notes for the Chapter:**

> Guys, sorry about the delay. 
> 
> Some serious stuff in my life has happened and threw me a little bit. 
> 
> Anyway - heres 9 - 10 is written and will be up in a few days time. Give everyone a chance to catch up with this one! :)
> 
> Enjoy!
> 
> -Winchest09

As Dean stirred awake in his large, queen sized bed, his cock throbbed under the sheets. His eyes hadn’t even opened and the first thought in his mind was the thought of fucking Y/N into the couch they were both sitting on last night. He wanted her riding him, he wanted her beneath him; he wanted to see her perfect, red lips wrapped around his cock as he fucked her mouth. He let out a low hiss as his large hand came to wrap around his length, his thumb grazing over his velvety tip as he smeared what precum had beaded around the head. He had already masturbated over her when he came to bed last night, imagining how it would feel to coat her walls in his cum, how it would feel to have her pussy clench around him as she came.

“Dean?” Sam’s voice sounded through the bedroom door, followed by two sharp knocks. Dean immediately threw his head back and let go of his cock, a frustrated growl leaving his lips as he sat up in bed.

“Son of a-” he muttered under his breath, throwing the covers off of his naked body as he walked over towards his dressing robe that was hanging over the back of a chair.

“You decent?” Sam shouted through the wood again making Dean roll his eyes in annoyance as he tied the cord of the robe around his waist.

“Does it matter?” he mumbled under his breath as his bedroom door started to open. Dean put on a wide smile and turned to face his little brother. “What’s up Sammy?” he almost sang, crossing his arms over his chest. When Sam walked into his bedroom, he grimaced, his nose crinkling slightly.

“Jeez dude, open a window. It smells like something died in here,” Sam cringed. Dean just huffed and loosened his arms as he walked over towards the window, drawing back the curtains and unlocking the hatch to let in some fresh air.

“Something did. My sex life,” Dean retorted, leaning against the windowsill as he stared towards his brother.

“Dean, it’s been what…four days?” Sam scoffed as he slowly walked towards his older brother. Dean’s face relaxed slightly at Sam’s statement. Had it really only been four days? Is that how long Y/N has been with him? He groaned slightly under his breath, he had yet another three weeks of her tormenting him. The previous conversation from last night, the bet he had made with her was in the forefront of his mind. He just knew he wasn’t going to last. His dick got easily hard, no amount of self-service was going to provide him with the relief he needed. It was like trying to get drunk on alcohol free beer.

“Long enough,” Dean complained with a huff but Sam just shook his head, an unimpressed look on his face. Dean knew he wouldn’t get any sympathy from his brother so he pushed himself off of the windowsill and walked over to his wardrobe. “Anyway, I’m sure you’ve not come here to talk about the pussy I’m missing out on. What’s up?” he questioned as he glided one clothes hanger along the rail, deciding on what to wear.

“Benny has just filled me in on what happened yesterday with Crowley,” Sam started, “that we got the deal and things are back on track. Is that true?” he questioned, his hazel eyes boring into Dean as he turned around.

“Yes it is, little brother,” Dean replied with a smile, “negotiations were made and a regular deal has been put back into place. We’re taking over a shipment of weapons next week,” he informed as he went back to sliding through the shirts hanging in his wardrobe.

“I’m also assuming Y/N played a huge part in it?” Sam asked and Dean stopped his movements, turning around to look directly at him.

“What if she did? I told you that’s what I hired her for,” he replied, his tone sharp. He saw how Sam’s expression changed to one of worry as his chest heaved with a deep breath.

“Dean, if she can help us get deals like this then great. My only concern is what’s going to happen when she inevitably leaves. People will start asking questions,” Sam worried, his brows knitting together. Dean shut the doors to his wardrobe in a huff. In truth, he hadn’t even thought of Y/N leaving, he hadn’t thought that far ahead.

“Sammy, for once in your life would you just trust me? Who said she’s going to leave?” Dean smirked before walking over to his chest of drawers. He saw in his peripheral vision how Sam was shaking his head at him in disbelief.

“You signed a contract Dean, with her and The Hemlock. She has to go back in three weeks,” Sam reminded him, a stressed tone to his voice.  

“Just like rules, contracts are made to be broken, Sam.” Dean smirked, thinking back to the previous night and the words exchanged between him and Y/N. Pulling open his drawers, he grabbed a pair of swimming trunks and started to change into them.

“What was the point in having me waste my time on creating a contact for Y/N and you, if you’re just going to break it anyway?” Sam huffed, a grimace on his face when his brother bent over in front of him. Dean pulled the trunks over his thick, bow legs before he rearranged his robe over them.

“Who said I’ll be the one breaking it?” Dean raised his eyebrows once in a suggestive manner, a small smile on his lips as he walked over to his door and held it open, hoping Sam would take the hint to leave so he could continue with his day. “Now if we’re done here, I’m going to grab some breakfast then go and relax in the hot tub.”

Sam just rolled his eyes and held up his hands half-heartedly in surrender before taking his leave. Dean followed shortly after, heading in a different direction towards the kitchen to line his stomach before his relaxing day ahead. Sure, he should be in his office working on his contacts and hatching new plans, but today was a day that he wanted to himself. Besides, who said he couldn’t work from the hot tub?

As Dean’s bare feet padded down the stairs, he was singing quietly to himself, his hands buried deep in the lining of his robe as he entered the kitchen. The smell of pancakes and bacon instantly filled his nose and he felt his mouth begin to salivate, his hands automatically reaching into the cupboard for a plate whilst Magda, the cook, smiled pleasantly as she plated up his breakfast. He thanked her before heading over to the open plan dining room that was positioned to the side of the kitchen, a long mahogany dining table positioned in the centre. As he got closer to the table, a redhead came into view and a grin graced his lips.

“Morning, Charlie,” Dean sang as he came to sit at the head of the table which was to the right of her. He placed his plate down before he eagerly started to dig into his breakfast. Charlie frowned slightly at Dean’s chipper tone, it was unlike him to be so happy in the mornings.

“What’s got you so happy?” she questioned, picking away at her toast as she glanced between him and her laptop screen that was set up in front of her. Dean continued to grin as he picked up a piece of bacon with his fingers.

“Deal with Crowley went well, I have pancakes and bacon for breakfast and I’m about to go and chill in my hot tub. I’m just missing my beers,” he mumbled through food filled cheeks just as Magda walked in with a pot of fresh coffee and a bottle of beer for Dean, “Oh no, wait, thank you Magda.” He took the beer graciously off of his cook before popping open the cap and taking a generous swig to which Charlie rolled her eyes.  

“Dean, it’s eleven thirty in the morning,” she scolded slightly, not wanting to step out of line.

“Well it’s happy hour somewhere.” He shrugged casually, wiping at his mouth with the back of his hand before placing the bottle on the table, nodding over to her laptop. “What you working on?”

“I’m still looking into, that  _thing_ , for you,” she replied in a hushed tone, looking over her shoulder to see if Magda was paying attention before going back to typing on her keyboard.

“What? What thin-oh,” he realised aloud as he shuffled in his seat slightly, “you, erm, you find anything?” he asked, going back to the rest of the pancakes and bacon that were going cold on his plate. In all honesty, with everything that had happened between them last night, he had completely forgotten that he’d asked Charlie to look into her twenty four hours previously.

“No.” She shook her head as a long sigh left her lips, “and that’s exactly my point,” she continued, deadpanning over to Dean as she threw her hands up slightly in exasperation. But Dean just frowned as he took in what Charlie had said.

“I don’t understand. Finding nothing is a good thing, it means there’s no skeletons hiding away that could harm the business,” Dean explained, wiping his hands on the napkin that was placed at the side of his plate as Charlie shook her head. She wasn’t convinced.  

“She’s  _too_  clean, Dean,” she debated, going back to look at her screen and all the evidence she had found on Y/N so far. “Think about it. The kind of work that she’s in, are you really telling me that she’s been squeaky clean all the way through? She’s not even had a tap on the wrist?” she prompted, a hand coming to run through her red locks as she did.

“She’s not your everyday prostitute, Charlie,” he tried to reason, thinking back to when he first went to meet Balthazar. He didn’t just pick her up off the streets, she was in a high ranked establishment and the amount of money he paid for her certainly suggested that she was more than just a street walker. Charlie just shook her head, she still wasn’t convinced, and her finger that was consistently tapping on her keys told Dean that.

“Look, I’m going to keep digging ok. By the end of the week, I’ll know past boyfriends, jobs and addresses. Just, play it safe alright? My gut is telling me that there’s something more here,” she stressed and Dean just nodded, picking up his dirty plate and half-finished beer and heading back into the kitchen. His previous happy mood had been dampened slightly by the reality check Charlie had just given him. So, he opened up the refrigerator and grabbed some more beer before making his way to the pool area.

It was a room that was quite open, floor to ceiling windows that lead all the way around giving anyone the perfect view of the private gardens. Tiled steps lead down into the pool area, to Dean’s right was a large, steam room with wooden interior. A single glass door was the only entrance. To his left was the large pool, half circle stacking steps leading into the water and right at the end, was the large hot tub that looked over everything else. Beers in hand, his bare feet padded along the tiles, the sound carrying in the quiet as he started to strip himself of his robe. Leaving it in a puddle by the hot tub, he slowly submerged himself into the warm water, leaving his beers in the conveniently placed cooler to the side of him.

As Dean relaxed back into the hot tub, bubbles popping around him creating a relaxing foam, he couldn’t help but let his mind wander back to what Charlie had said about Y/N. She had got a point, being in her line of work there was bound to be a few black marks against her name but then again, if Y/N knew the right people, anything could be made to go away for a price. So did that mean she  _was_  hiding something? He shook his head as he took a long sip from his beer bottle, if she was bad news, surely he’d catch on. She was eager to help him, not biting off his hand for money when he took her shopping, she seemed genuinely grateful for the way he was treating her. Was he letting his  _near obvious_  attraction to Y/N cloud his judgement here? Could it be that she really was hiding something?

A sudden splash made Dean’s head snap up as he stared out across the pool. He saw a slender figure glide underneath the water and he raised an eyebrow. Soon enough, the figure broke the surface of the water to reveal that it was Y/N, clad in a black bikini that left little to Dean’s imagination. He ticked his jaw slightly before taking another long sip from his beer, his green eyes trained on her figure as she slowly pushed the wet hair from her face to rest her hands at the nape of her neck, her Y/E/C eyes catching his before she slowly turned away from him in the water. Dean continued to watch her as she did slow laps in the pool;  _she even swam elegantly._

After a few laps, Y/N stopped at the end of the pool and started to climb the stacked half circled stairs out of the water. Dean watched on eagerly, as the water slowly trickled down over her skin of her back. As her full body came out of the water, he watched as she traced her delicate hands down her sides to the curvature of her hips, fingers running down under the bikini material to rearrange the bottoms, giving Dean a perfect view of her pert ass. He inaudibly groaned, she knew exactly what she was doing and the look she gave him over her shoulder confirmed it. At this point, his dick was throbbing, once again. All Dean could think about was bending her over there and then and fucking into her as hard as he could. He wanted to make her scream, he wanted to make her cum so hard that she would be seeing stars for the next week.

But he couldn’t.

“Fuckin’ contract,” he muttered under his breath as he threw his head back to try and regain some sort of composure. He couldn’t let her see that she was getting to him, he knew how desperate he was going to look. But no matter how hard he tried, his hard cock that was resting against him was not going away. Instead, he lifted his head and slowly, with his free hand, slipped it into the bubbling water and underneath the band of his shorts. His eyes were fixed on Y/N as she slowly walked towards him, her wet breasts bouncing slightly with each step she took. Dean sucked in a breath as he encased his hand around his length, pumping slowly, just for some relief.

“You alright, Dean?” her soft voice cut through to him as she came to stand at the edge of the tub. Immediately, he withdrew his hand and rested it on the back of the hot tub, the other circling the bottle of beer as he studied YN.

“Never better, sweetheart,” he replied, smoothly to which Y/N smiled and turned back around. With a wet hand, Dean rubbed down his face. He had never let a woman get to him like this before, but then again, he’d always managed to find some pretty pussy to stick his dick in.

His eyes were once again fixated on the slender body in front of him. He knew Y/N had deliberately stood where she had so he would get the best view of her body as she stretched her limbs. She bent herself to each side slowly, giving him an excellent view of the side of her breasts before she decided to bend forward, her hands grazing down her legs as she came to a stop at her tiptoes. Now all Dean was faced with was her perfect, curvaceous ass that he was just dying to spank. She wiggled side to side slightly, an almost orgasmic moan leaving her lips as she stood and rolled out her muscles.  _Fucking tease._

Dean continued to watch, finishing off his beer, as she placed her arms above her head and got into the diving position. Within seconds, she’d pushed off the side of the pool and dived into the water. Dean just shook his head, her form and how she dived was all wrong, but he knew she knew that. Y/N was swimming elegantly before, knew everything about everything, so he highly doubted that she could get diving wrong.

“That’s not how you do it,” he stated as her head emerged from the water, a small smirk on his lips once more. Y/N just raised an eyebrow at him, mirroring his smirk.

“Oh really?” she replied innocently, slowly pushing herself backwards through the water as she looked up at him, “how about you come and show me how it’s done?” she teased and Dean let a short sharp breath leave his nose.

“I’d much prefer to show you my other talents, Y/N,” he confessed, his voice as smooth as honey, “but for now, I’m just enjoying the view.” With that, he sunk himself a little lower into the tub, enjoying the warmth it was providing him as he continued to watch her as she made her way out of the pool, wiping the wet hair from her face.

“And here’s me thinking you can handle a woman when she’s wet,” she purred, picking up her towel from the nearby lounger before she began to dab at the beads of water that were trickling down between her breasts. “Is this bikini a little too much for you?” she asked teasingly, pulling the towel away from her body and to her side before she dropped it to the floor, her eyes never leaving Dean’s. “because there are always ways to…remedy that,” she confessed, turning around as she undid the string of her bikini top. Dean swallowed hard as she slowly peeled the wet material from her skin, dropping it onto the towel next to her before she teasingly swayed her hips as she slid her bottoms down her legs, leaving them where she stood. She glanced over her shoulder once more at Dean, who was gripping tightly to the side of the hot tub, before she entered the steam room.

“God fucking dammit,” he growled, running wet hands through his hair and down his face. She was good. She was very fucking good. His demeanour was faltering, his cock was twitching painfully hard his swim shorts but he wasn’t about to fall at the first hurdle. As much as he would love to follow her into that steam room and to sink his cock into her, it was  _against the rules._  Dean needed Y/N to be begging for him, he needed her to be a hot, dripping mess, just pleading with him to fuck her. So he needed to show her, exactly what he was made of. It was time to up his game.

Leaning over the side of the hot tub, Dean grabbed his robe and pulled out his phone. Using his fingerprint to unlock it, he scrolled through his contacts, going through a long list of women’s names. He was mentally checking off certain ones as he went, he needed the right woman, someone that would play his game without them even realising it. He stopped at a name and with a smirk resting on his lips, he dialled the number.

“Lindsey, baby, how are you?” he sang down the phone, his eyes trained on the glass door Y/N had gone through. “I’m good, just sitting here in my hot tub thinking how good your pussy felt wrapped around my cock, thinking about how good you tasted…” he husked, listening to how she was mewling to him on the other end of the phone. “You free today?” he questioned, his hand snaking back into his shorts to wrap around his cock as he thought of Y/N naked in the steam room just metres away. He needed release and when he heard how eagerly Lindsey accepted his invitation, his smirk broke into a grin.

“Perfect.”


	12. Chapter Ten

**Notes for the Chapter:**

> Enjoy chapter ten guys! 
> 
> Please don't hate me :') 
> 
> \- Winchest09

Y/N bit into her lip softly as she lay naked along the wooden benches in the steam room. She felt exhilarated and for the first time in a long time; sexy. She wondered if this is what it would feel like in a relationship. To feel beautiful, to feel wanted, to feel like something more than just an escort; to feel like she belonged. She knew she’d never experience a real relationship, how could she? Her life was dictated to her, rules and regulations stopped her from doing anything  _normal._ However, she didn’t care at this moment in time about her rules and regulations because she was here, in this manor, with Dean. Someone who wanted her for her brains and her skills outside of the bedroom and that was something she had never come across before.

She stretched her arms above her head as she thought more about Dean, the way he looked at her, the way he spoke to her; god did she want him. He made her feel desirable and the ache between her legs proved it. She secretly hoped that her previous strip tease had been enough to tempt Dean into following her in there, that it had been enough to make him want to fuck her senseless. She saw how he reacted to her teasing. She knew he thought she hadn’t noticed how his hand was under the bubbles, how he was looking at her with parted lips. She knew his hand was wrapped around his cock and she loved that she did that to him. She just needed to push him over the edge.

Knowing that he could see her at any point, naked through the glass door, gave her a thrill and her pussy throbbed. Her hands slowly came down from above her head as she caressed her breasts, pushing them together and teasing her nipples with her fingers. God, how she  _needed_  him. She needed him to come into this sauna and run his stubble down her body, she needed him to feel how wet she was for him, she needed to feel his hard cock inside of her as his fingers rubbed at her clit. In this moment, she hated the fact that there was a no sex clause in her contract with him.

It had been over a week since she’d had any kind of sex with a man, even longer than that since she’d had  _satisfying_  sex. A lot of the time with past clients, she had resorted to fixing herself as they hadn’t cared about getting her off.  As she lay there, incredibly sexually frustrated with one hand kneading her breast and the other between her legs, she knew she needed more than just her fingers.  She hurried to sit up and stand; she was going to face Dean naked, let him take in everything she had to offer before heading to her room to find and use her sex toys. She wasn’t about to go begging him for it if he hadn’t moved.

As she peered through the steamy glass door, she noticed how the hot tub was now empty and a disappoint twang resonated through her chest. Her arms subconsciously crossed over her body, the feeling of not being enough threatening to take over her as she rushed to grab her towel. The earlier feeling of being sexy and wanted was fading. Y/N quickly wrapped the towel around her body before she grabbed her wet bikini and made her way to her room. The manor was quiet and she was thankful that she hadn’t bumped into anybody along the corridors as she rushed towards her bedroom door.

Once inside, she leant back on the wood and let out a big sigh. She’d never before met a man with so much restraint, normally they couldn’t wait to rip her clothes off and get themselves off by using her. Dean was different, and it was frustrating. She threw her wet bikini into the bathtub in her bathroom before undoing her towel and turning on her shower. The earlier throb she was feeling had dulled and when she walked over and opened the drawer where her sex toys were kept, she turned up her nose. She just wasn’t feeling it anymore. Before she slid it closed however, she noticed her burner phone that she had been given for this contract flash with notifications. She knew exactly what messages would be waiting for her and she swallowed hard, pushing down the bile that was threatening to rise in her throat.

 **From:** M

11.35am:  _I hear no complaints from this contract, Y/N. In fact, you’re quiet. What have you been told about checking in? You have 24 hours to respond, or else you know what happens._

_M._

Y/N took a deep breath as she held the phone in her hands. She wondered when she would hear from The Master, from  _him._  He’d never been able to just let he go anywhere without his knowledge, she’d never been able to be free of him for a single day. Taking a deep breath, she typed out her response, hoping it was enough.

 **To:**  M

12.45pm:  _Sorry, Master. Been busy, Sir. Everything is fine. Gentlemen is satisfied._

_Y/N xx_

The fact she had to put kisses after her name made her stomach churn. She refused to do it once which made The Master very angry. He had told her that she was his girl, that he owned her and as she was his, she should show him some gratitude and affection for everything that he does for her. Y/N tapped the phone against the palm of her hand as she walked back towards the bathroom, intent on taking that shower. As soon as she placed the phone on the counter, she heard it buzz along the marble.

 **From:**  M

12.47pm:  _Hmm, good. Keep up the good work, make sure you leave him coming back for more. Repeat business is the best business. Be my good girl, now._

_M._

The end of his message instantaneously took her back to the day he’d called her his  _good girl_  for the very first time.

_Nine years ago:_

_The room was cold and dark, the familiar smell of concrete surrounding her as she counted that today was her seventh day in isolation. Her last day. She knew this by the amount of servings of cold porridge she had been given, and the fact she was allowed one glass of water a day and she had finished her sixth hours ago._

_Y/N shivered in the corner of the room, her arms wrapped around her naked frame as she tried to huddle for warmth. The Master knew what he was doing when he chucked her in here, her ribs littered with bruises. He kept the temperature just warm enough to where she wouldn’t fall ill but cold enough that she’d feel uncomfortable. He also knew just how hard to hit her to not cause any broken bones, only bruising. She might have stepped out of line but The Master was smart enough to not put her out of service for long. In his mind, a week was long enough and if she still acted out, he’d get creative with his punishment._

_For the first time in a long time, Y/N was fearful of what The Master might do to her. She had tried to sneak out of The Hemlock in a bid to go to the movies. She’d heard that one of the other girls had been with a client to see a film and she so desperately wanted to experience what it was all about. She wanted to see the lights and smell the buttery popcorn. She wanted to see something other than the same four walls of her room. But The Master had caught her, even when she thought she had outsmarted him. His henchmen had come marching into the theatre, spotting her by the popcorn stand as she handed over what little money she had in her purse to buy her snack. They approached her quickly and inconspicuously, pulling the popcorn from her grasp and throwing it into the bin as they escorted her out of the theatre and back to The Hemlock. She never even got a taste. She could never be free._

_The sound of the metal door squeaking to open instantaneously made Y/N lift her head from her knees, her eyes squinting at the bright light that was now filtering in her room from the open doorway. She fidgeted slightly, waiting for her orders or another plate of cold food to be delivered. However, when a dark figure entered her room, hands in their pockets, she cowered slightly. She knew exactly who it was._

_“Come with me, child,” he ordered, turning on his heel and leaving the isolation chamber. He didn’t have to ask her twice, she’d do anything for some clothes and to feel the sunshine on her skin._

_She followed obediently, her head bowed as she walked down the corridor. She could feel the eyes on her as she walked. Daring to look up from the carpet, she was right. She saw the judgemental eyes of The Master’s men and the empathetic ones of her fellow girls. They all knew where The Master was taking her; back to his office to set things straight. As they entered the elevator, Y/N stood quietly next to him, her hands by her sides, fighting the urge to cover herself as she felt his eyes roam her figure. She could only breathe a sigh of relief when she heard the ding of the elevator signalling that they were at his office._

_He motioned for Y/N to follow him with a flick of two fingers, an action she obeyed before she was told to sit on the floor, facing the couch. She heard the clink of a glass bottle against a glass and she knew he was fixing himself a drink, she wasn’t leaving anytime soon._

_“You broke the rules, young lady,” his voice echoed around his office, making Y/N wince slightly as he spoke._

_“Alastair, s-sir, sorry-” she stumbled over her words, playing with her fingertips “-it-it was a mistake,” she stumbled over her words._

_“You’re right there, mmm, it was a mistake,” Alastair taunted, swirling his drink around in his glass as he walked to stand in front of her, stooping slightly as he forced her to look up at him. “Now how are you going to make it up to me?” he questioned, his eyes flickering between hers and her lips._

_“I…I don’t know, Sir,” Y/N stuttered, breaking eye contact with him as soon as Alastair released her chin._

_“Oh, come now child, you’re smarter than that,” he said with mock disbelief, “that’s why I like you, you think outside of the…mmmm…small box,” he taunted, a small laugh leaving his lips. Y/N just continued to look at her fingers, not liking where this was leading._

_“I can only apologise once again, Sir,” she offered, her voice quiet._

_“Apologies, apologies,” he sang, placing his glass down on the end table before coming to stand back in front of her, “they only get you so far in life, I need you to prove to me that you’ve changed, Y/N. That you’re enjoying your stay here with me,” he explained, tucking a stray bit of her dirty hair behind her ear, “but when you disobey my orders, sneak out and break the rules, it sends a very **different**_ _message.” His fingers pinched at her chin, holding her head in place as he forced her to look at him. Her eyes went wide as they scanned his, flickering from one to the other._

_“I promise I won’t do it again,” she begged, her eyes beginning to glass with fear of what he was going to do to her._

_“And how can I believe that?” he asked, finally releasing her chin from his grasp. “Oh, I know. Show me how much you love me, dear. How grateful you are for how I treat you.” His cold hands started to slid down her skin, his rough fingers tracing over the side of her breasts and she was doing all she could to not whimper._

_“I…I don’t know how,” she confessed, feigning ignorance and hoping he’d come up with another punishment._

_“Oh I do,” he smiled wickedly, his hand coming to a stop on her skin before he stood abruptly. The sound of his belt buckle coming loose made her squeeze her eyes tightly shut, she tried to fight the grimace that wanted to grace her face. She heard how his button popped on his trousers, she heard the slow metallic sound of the zipper lowering on his fly. She then watched as he lowered himself to the couch behind him, she saw how he was almost hard, working himself up fully by looking at her, his fingers from his other hand coming under her chin to force her to look at him. After a minute had passed, Alastair’s hand left his length and rested on the arm of the couch._

_“Go ahead,” he taunted, a malicious grin on his face as he gestured towards his cock, looking down at the naked girl at his feet, “be my good girl, now.”_

Y/N couldn’t hold it in any longer, the bile that was sitting in her throat rose and she emptied the contents of her stomach into the toilet. She hated him and for what he had done to her, even though the words weren’t spoken, they still erupted the same nauseous feeling from within her. Wiping at her lips, she pulled on the flusher before heading over to the sink to rinse out her mouth. 

She slowly stepped into the steaming shower, turning to press her bare back to the tiles before she slid to the bottom, hugging her knees as she let the water fall over her skin. She stayed there for what felt like an hour. She hated Alastair, she hated herself; she hated everything there was about this life. Since that day, she always strived to be the best. She never wanted to go through a punishment like that ever again. Beatings she could deal with, isolation she could deal with but what Alastair made her do? She couldn’t. Even now, after six years of training, she was still haunted by the way he felt on her tongue and the look on his face when he’d finished.

Then it dawned on her what The Master had said over text.  _Keep him coming back for more._ She had to up her game, she had to make herself desirable enough for him to want to keep her around, for repeat business. She stood up in the shower and quickly washed through her hair, making sure everywhere was clean shaven before she left the bathroom. She used the best moisturiser on her body to make her skin smell incredible before opening her underwear drawer to find the most extravagant that she could. She then pulled out a mid-thigh pinstripe dress with heels to match before sitting down at the dressing table to begin styling her hair and applying her make up. She was determined to make Dean break the contract, she needed to show him just how  _good_ she could be.

Once she’d finished getting ready, she glanced towards the clock on the wall and noted it was nearly half five in the evening. With it being nearly dinner time, she thought that Dean could be getting ready for the evening meal in his room, so that’s where she decided to stop by first. She left her bedroom and with a sway in her hips, she walked swiftly to where she remembered his room was.

Two gentle rasps on the door later, she was waiting by his door for him to open it. However, she was only greeted with silence. With a frown, she knocked twice more, this time leaning her ear closer to the door to listen for any sound of him. Nothing. Y/N didn’t think much of it, he could already be downstairs. To get there, she’d have to pass his office so she’d check there too. When his office proved empty, she took the door that led to the outside veranda which in turn led to the kitchen. As she neared, she saw figures sitting around the island in the middle of the room and her hope rose in her chest that Dean would be there.

Her heels clicked against the floor were what made the gentlemen look up and in her direction, her heart dropping in her chest slightly when she saw that Dean wasn’t there. In fact it was just Benny and another man that she hadn’t had the pleasure of meeting.

“Evening, ma’am,” Benny greeted, nodded slightly towards her and Y/N walked towards them.

“Hi, Benny,” she replied, smiling politely before her eyes landed on the blue eyed boy who was drinking from a glass of water. He quickly swallowed and wiped his hand on his suit before holding it out towards her.

“Oh, I’m Castiel but please call me Cas,” he introduced and Y/N had to bite back a chuckle at how adorable he was.

“Evening, Cas. Lovely to meet you,” she said softly, taking his hand and shaking it. “I don’t suppose either of you have seen Dean lately?” she asked, a little hopeful that he wasn’t too far away. She noticed how Cas and Benny shared a look and it made her frown slightly.

“He went into the swimming pool area about half an hour ago,” Castiel answered and she nodded with a smile as a thank you.

“Aren’t I a lucky girl? Get to see him wet and naked twice in one day.” She winked towards the men before she turned on her heels and headed towards the pool. A devilish smile graced her lips, if he was in the hot tub again, she’d strip down to her underwear and join him. It was an idea that excited her greatly.

Y/N pushed open the door to the swimming pool, her heels echoing around the room as she looked around for the green eyed Winchester. Automatically, her eyes fell on the hot tub, considering that’s where he was this morning but she found it was empty as she walked down the steps. She looked at each lounger and even to the outside area to see if he was maybe getting some last minute sun, but to no avail. She was about to turn around and head back to the kitchen when the sound of a low growl filled her ears, it made her stop in her tracks. Her eyes landed on the steam room, a place she hadn’t thought of checking.

“Dean?” she called out softly, her voice carrying in the empty space. There was no response to her call, just another grunt which was then followed by a high pitched squeal.

Her heart sank to her stomach. She was hoping she wasn’t hearing what she thought she was. She braved another step closer, her eyes trained on the glass door, each step she took allowed more of the steam room to come into view. Another moan, a  _female_ moan. One more step was all it took for Y/N to find Dean, balls deep in another woman.

She should have turned around, she should have given them their privacy but the sounds he was making and the way he had his hands wrapped around the woman’s body, was everything she’d pictured for herself only hours ago. Dean was sat on the wooden benches, the blonde’s legs wrapped around him as she bounced enthusiastically up and down on his cock. He had his lips buried into her neck, sucking and biting at her pulse point as one of his hands came around from her back to her breast, kneading it. Y/N was about to look away when Dean looked up, and through the steam, caught her gaze.

However he didn’t stop, he continued to fuck into the woman, angling himself lower so she could fuck him harder from the top. He kissed along the woman’s shoulder, his eyes never leaving Y/N’s as he did so. She’d tuned out of the woman’s moans of his name, all Y/N could do was watch as Dean came undone inside of the random woman he was fucking. It was in that singular moment, when he squeezed his eyes shut and his fingers pressed into the woman’s skin a little harder, that she knew she’d failed.

She turned on her heels and walked briskly out of the pool area, her heels clicking violently on the floor as she made her way to the hallway and up the grand stairs. As she stormed towards her bedroom, she was fighting back her tears, she felt so stupid. Her earlier thoughts of being wanted, and being desired were based on lies. Y/N shook her head as she flung open her bedroom door, quickly shutting it and locking it behind her before collapsing onto her dressing table chair. She looked into the three way mirror that stared back at her and she scoffed. Why would he ever want her?

Y/N didn’t bother to wipe the mascara that had run down her cheeks as she continued to sob. She knew this was going to reach The Master back at The Hemlock, she knew her punishment was inevitable. The Master’s words from earlier were circling around in her head.  _Make sure you leave him coming back for more._  He’d gone somewhere else instead, he had chosen a random woman over breaking a contract with her. She had failed to keep her client interested after only four days, she’d failed to make him want her over anyone else and she’d failed to keep him happy.

She’d failed. 


	13. Chapter Eleven

**Notes for the Chapter:**

> Guys!
> 
> Oh my god, someone needs to give me a good shaking. I honestly thought i posted this on Saturday like i said i would...but i didn't press post *facepalm*
> 
> Anywho...sorry its late! Haha. 
> 
> Enjoy!

Dean tried to focus on the feeling of being deep inside of Lyndsey, the blonde woman he had booty called hours earlier that day in a bid to make Y/N jealous. But something felt different, something felt off. He wasn’t getting the same buzz that he was used to getting. Sure, she felt good wrapped around him, her nails clawing into his skin and her breasts bouncing in front of his face but he still found his mind going back to Y/N. She hadn’t yet seen him with Lyndsey which was something Dean was a little frustrated over. As soon as his booty call arrived, he had hurriedly ushered her into the swimming pool area, hoping that Y/N would still be in the steam room but she had gone. However, before Dean could say anything, Lyndsey had wrapped herself around him, placing her pink stained lips onto his as she dragged him backwards into the steam room. He submitted to her advances of course, wanting to let off his own steam and frustrations but it didn’t seem to be working.

Eager to get himself off, Dean buried his face into Lyndsey’s neck as he tried to concentrate on the feeling of her pussy pulsing around his cock. He brought his lips to her neck, nibbling at her pulse point which made her squeal loudly and encouraged her to ride him harder. He brought his hand around from her back, graced it across ribs before he brought it up to her breast to squeeze it slightly, pinching her nipple between his fingers. As he continued to kiss her skin, his eyes glanced over to the door and through the steam, he swore he could make out the outline of Y/N. He let his lips break free of Lyndsey’s skin as he continued to stare through the glass door, and as the steam cleared a little, his eyes caught the piercing Y/E/C ones of Y/N.

He felt his heart speed up in his chest, he could feel it pounding against his ribs as his cock twitched inside of Lyndsey. He hadn’t banked on Y/N coming to look for him, he was just going to get his fill and move on but this, this turn of events could go in his favour. Maybe Y/N would see just how good he was at pleasuring women, maybe this would be the thing that broke her. With that thought in mind, Dean angled himself lower and started to fuck up into Lyndsey, his thrusts powerful and deep making the woman on top of him scream and her grip on him tighten. But he was still chasing his end, he was still so far from coming undone but Y/N didn’t need to know that. As far as Y/N was concerned, he was having a great time without her but he had to make it look more convincing. On that thought, he started to grunt, his fingers dug harder into Lyndsey’s flesh before he squeezed his eyes closed and feigned his orgasm.

The moment he opened his eyes, he focused them quickly on the spot where Y/N stood, only to realise she’d gone. He didn’t know what reaction he was expecting but the fact that she wasn’t stood there anymore bothered him somewhat. Had his plan worked? Had he made her jealous?

“Dean, baby, that was amazing,” Lyndsey praised, her lips nibbling at his earlobe as her voice brought him back to her.

“Uh huh,” was his simple response, his green eyes looking everywhere but at the woman who was straddling him. He placed his hands on her hips and started to gentle lift her off of him, shuffling himself out from underneath her as he reached for his discarded robe. He hadn’t noticed the confused look on Lyndsey’s face at his reaction and as she stood, fully expecting cum to be coating her thighs, she found nothing.

“Wait…you didn’t…you faked it?!” she shrieked, grabbing onto Dean’s forearm to force him to look at her.

“Surprise, doll. Men can fake them too,” Dean quipped, a sigh escaping his lips as he pulled his arm out of her grasp. He reached down to the floor and picked up her underwear, gently placing it on the bench between them without a word. It was a visual cue for her to get dressed.

“Am I boring you?” she asked as she frowned, slowly reaching for her underwear as she continued to stare Dean down. He rose to his feet, tying the belt to the robe around his waist as he looked down at the girl his dick was buried in just moments ago.

“No look, Lyndsey, I’m just not feeling it, alright? I’m sorry, I really am,” he admitted, his apology genuine as she continued to dress. He was telling the truth, he wasn’t feeling it. He didn’t know whether it was to do with Y/N’s teasing or how his brain was wired but tonight, Lyndsey just wasn’t enough. “I’ll get Garth to take you home,” he offered, walking towards the steam room door and holding it open.

“Next time you call, Dean. I might not come running. This may have been your last chance,” Lyndsey huffed, pulling her dress over her messy blonde curls before she grabbed at her shoes and stormed passed Dean.

“I’m sure I’ll get over it,” he mumbled under his breath so she wouldn’t hear as he rolled his eyes.

He followed her closely behind as she made her way to the front door, Dean was keen to ensure she didn’t have sticky fingers or looked at something she shouldn’t. He didn’t want to make the same mistake again just because he wanted to get laid. Without a word, he opened the front door for Lyndsey, watching as she walked down the stairs towards where Garth was standing with transport. Dean only had to give Garth a nod and a gesture and he knew exactly what it meant. When Dean knew that Lyndsey was secure in the vehicle, he quickly shut the door behind him and pinched at the bridge of his nose. He needed a stiff drink. Turning to walk into the kitchen, he was stopped in his tracks when he saw the stoic face of his little brother, sipping on a coffee.

 “Don’t start Sam,” he grumbled, pushing past him into the kitchen. Sam just shook his head as he slowly turned on the doorframe he was leaning on.

“Really, Dean?” he chastised, unimpressed that his older brother had yet another random woman in his bed, or the steam room in this case.

“I said don’t start, I know alright?” Dean snapped, slamming the doors of all the cupboards he was looking in as he searched for some whiskey. Finally, he found a bottle in the last one he looked in and pulled it out, along with a tumbler and slammed them both down on the kitchen island.

“Look I’m not about to give you a hard time over sleeping with someone Dean. It’s when you get reckless that I get pissed,” Sam said softly, pushing off of the doorframe to take a seat at one of the stools around the kitchen island.

“Yeah, well trust me. It won’t be happening again anytime soon,” Dean stated into his whiskey before taking a generous sip.

“That bad huh?” Sam asked, raising his eyebrows as his hands hugged the coffee mug. Dean just sat himself down opposite his little brother, his large hand running through his already messed up hair.

“Just same old, same old,” he admitted with a tired sigh. There was a moment of silence between the brothers. Sam sipping at his coffee and Dean nursing his whiskey while he thought over the past few hours.

“Did Y/N catch you with her?” Sam asked softly, sliding his now empty coffee mug away from him. Dean just frowned before swallowing the rest of the amber liquid that stung his throat.

“What makes you say that?” Dean arched a brow, wincing slightly at the burn of the whiskey as he moved to top up his glass.

“She rushed off up the stairs moments ago, couldn’t tell if she was pissed or upset or just in a hurry to get to her bedroom,” Sam uttered, shrugging his shoulders slightly as he ran a hand through his locks, his dark eyes trained on his big brother

“She walked in and-” Dean thought about lying for a moment but his face said it all, “-yeah she saw me fucking Lyndsey. Eye contact and everything,” he sighed, running his large hand across his stubble before bringing the now full glass of whiskey back to his lips.

“What are you doing, trying to make her jealous?” Sam scoffed. “How old are you?” he teased causing Dean to roll his eyes at his brother’s jibe.

“Look, I fucked up alright? Didn’t think it’d go the way it did,” he admitted honestly, holding his hands up slightly in surrender, his green eyes not wanting to focus on anything other than the glass in front of him.

“What you thought she’d strip naked and come and join you?” Sam chided, a small smirk on his lips at how truly dumb his brother was being. Dean just let out a frustrated huff, his hand rubbing at his brow before finally looking Sam in the eye.

“I’ll make it up to her alright? I’ll figure it out,” Dean grumbled, “somehow,” he muttered, leaning back down onto the counter to once again sip at his drink. He looked to see Sam smirking at him, his fingers tapping the marble of the kitchen island slightly before he stood, shaking his head.

“Dude, if you like Y/N, just go and tell her. Ask her out on a date or something,” Sam coaxed, tucking the stool back under the island. Dean almost choked on his drink, coughing and spluttering as he covered his mouth.

“Woah, who said anything about liking her? Sure she’s fit as fuck, clever and man does she have a way with words but she’s here to do a job and that’s as far as this goes,” Dean spilled, shaking his head in disbelief at the words that had left Sam’s mouth but his little brother could see right through his façade.

“Whatever, Dean. Just don’t try to buy her,” he advised before he walked out of the kitchen, leaving Dean all alone with his glass of whiskey and his thoughts.

“I already have,” he whispered, running his hands through his short tousled hair as he stayed seated at the island. Was Sam right? Did he have more than just sexual feelings for this woman? She hadn’t even been with him for a week and he hardly knew a thing about her. Y/N was an enigma to him and to the rest of his family, not even Charlie could find out a backstory on her, not yet anyway.

Maybe he was playing this all wrong, sure they made a bet of who could break who first but maybe he needed to approach her from a different angle. As he drank the rest of his drink, he left the glass on the side and started to walk towards his room, contemplating his thoughts. He wanted to get close to her, he wanted to at least know what her favourite pizza topping was. It wouldn’t be much, but it would definitely be a start. If he couldn’t get her into bed by sexually teasing her, he’d woo his way in by romancing her. Either way, he was going to win this bet.

-

The next morning, Dean was up around his usual time after a little lie in and some self-love. He’d showered, shaved and styled his hair before dressing himself in a loose white shirt and dark suit paints. Today was a brand new day and the first thing on his agenda was to make things up to Y/N. He didn’t know where he would start or even how she was going to be with him but he had to take this step in making things right. His first thought landed on breakfast and how he wanted to personally deliver her fruit bowl to her that morning. So with a plan in mind, he raced to the kitchen to ask Magda for Y/N’s usual. He hadn’t expected Magda to shake her flipper at him as she informed him that Y/N didn’t have dinner last night and that it was his responsibility to ensure she was fed. _She’s all skin and bones._ Dean was concerned to learn that she hadn’t had anything to eat the previous evening and the overwhelming feeling of guilt threatened to swallow him as he sat waiting for Magda to pass him Y/N’s breakfast. Had he really upset her that much that she refused to eat? Surely that couldn’t be right, there had to be more to it and it was something he was determined to find out.

With a fresh bowl of varied fruit in hand, Dean walked promptly along the corridor towards Y/N’s room, his stomach turning as he got closer. He had no idea how this was going to play out and it was something that terrified him. He wasn’t scared of attempted assassinations or the thought of dying, he wasn’t scared of being caught by the cops or ambushed by a rival mob but he was scared of the wrath of a woman. His mother had taught him a lot of things and that but her wrath was something that always stuck with him. She never shouted or stomped around, she never screamed at him or clocked him around the ear. She stayed silent, an odd word here or there and that was more than enough. He would have much preferred the clock round the ear to a few days of silence from his mother.

Clearing his throat, he raised his hand and knocked twice upon Y/N’s door, waiting patiently for her to open. He listened as he heard a few thudded footsteps pad closer towards him and he tried to swallow down his nerves. When the door swung open, he felt like he was a deer in the headlights. Y/N was dressed in a tan summer dress, her hair neatly curled and her make up subtly done. She looked beautiful. It took a while for his brain to kick back into gear.

“Morning, sweetheart,” he sang, a wide smile on his lips as he looked straight into her eyes however his smile dropped slightly when it wasn’t returned.

“Dean, good morning,” she replied professionally, before turning around and walking away from the door. He frowned slightly, the guilt creeping up on him once more as he cautiously followed her into her bedroom.

“I’ve brought you some breakfast,” he stated, pointing towards the bowl of fruit in his hand as he shut the door behind him with his foot. Y/N just turned briefly, tucking some stray hair behind her ear as her eyes landed on the bowl.

“Oh, thank you but I’m not hungry,” she uttered, before sitting herself back on the bed on her knees, surrounding herself with papers.

“You need to eat, Y/N,” Dean scolded mildly. “I’ve been told you had no dinner last night and you’ve not left your room this morning,” he continued, placing the bowl of fruit on her dresser.

“That’s because I’ve been busy doing my job,” she somewhat snapped, looking up briefly at Dean from under her long lashes before glancing back down at her paperwork. “this is a plan to help get the Winchester name back out there,” she muttered, circling names and other important bits of information on the sheets in front of her.

“What?” Dean asked, slightly confused as he come to walk around to the side of her bed, his green eyes scanning over the different notes and pages strewn across her bedding.

“The Grande Gala that’s in a few days’ time,” she pointed out as if it was obvious. “With a bit of researching, I’ve managed to acquire last year’s guest list. I then cross referenced that with what I know of the criminal underworld and I’ve worked out who we need to speak too, play off and do business with to ensure the Winchesters rise to the number one spot,” she explained, using her pen to point to her research that was surrounding her. Dean was astounded by the lengths she had gone to and it only confused him more that she’d done this after what had happened last night.

“Sweetheart, that’s-that’s amazing,” he praised, his hand coming up to grace her shoulder slightly but she subtly moved away from his touch. If he hadn’t of already been weary of how she was acting around him, he would have missed it.

“That’s my job.” Y/N shrugged. “Am I required for anything today or is your diary already full?” With the look that she gave him, Dean felt like he was winded. He needed to explain himself, he couldn’t let this go on. She didn’t even want his hand on her shoulder.

“Look, Y/N, about last night-” he began to explain, his hand going to the back of his neck as he scratched at it awkwardly.

“What about last night?” she questioned bluntly, her Y/E/C eyes staring into his which made him swallow hard.

“Lyndsey, the woman I was with,” he continued, bringing his hand down from his neck to his mouth to which he rubbed. Y/N just broke eye contact with him, shuffling herself off of the bed and collecting all of the papers and putting them into one bundle in her arms.  

“Dean who or what you do in your own time is no concern of mine. You hired me to help your business grow, not to satisfy your sexual urges, right?” she sassed, reminding him of the terms of their contract before she turned and started to walk towards her dresser. He was a little thrown off, he hadn’t expected this reaction at all. To be honest, he didn’t know what to expect but he knew this wasn’t it. If he was honest, he also felt a pang of disappointment. Their usual flirty banter had been lost and he only had himself to blame.

“…right,” he drawled, wincing internally at her words. He had to make this right before the gala, he wanted to make things right. “Listen, I’d like to take you out this afternoon. I’m going to cancel a few appointments in my diary because I want to take you to this little formal boutique that my family owns. I need to get you fitted for a dress for the Grande Gala,” he explained and Y/N stopped in her tracks. She turned slightly, a few of her curls falling over her shoulder as she did so.

“Of course, I’ll be ready whenever you need me. In the meantime, I’ll continue to memorise my research,” she nodded and graced Dean with a small smile before she placed her papers down on the dresser. Dean stood, feeling just a little better about the situation as he started to walk towards her bedroom door, his hands in his pockets. Silence had fallen over the pair, Y/N was scribbling away in her notes and Dean was just watching her work. He had to give it to her, she certainly knew what she was doing and he had been shocked with how much research she had done in the past twelve hours. He wanted to let her know just how amazing she was at her job; he wanted to see her smile again.  

“Before I go, do you have any performance reports or anything I need to send back to The Hemlock?” he questioned, wanting nothing but to give her full praise for everything that she’d done. However, when Y/N fumbled with her pen and knocked some papers to the floor, he grew a little concerned.

“What? Why? Is there something you want me to do differently?” She asked urgently, a desperate look in her eyes as she stared at Dean. He didn’t know what it was but something about this look made his heart ache. How could she be worried about her performance when she was already knocking it out of the park? With a reassuring smile, Dean looked down at her.

“No, sweetheart, not at all,” he husked, opening her bedroom door. “You’re perfect,”


	14. Chapter Twelve

Y/N sat at her dresser, papers scrunched up in her hand as her eyes stayed trained on the back of the door that Dean had just walked through. The panic that was starting to rise in her body was beginning to simmer as she let his words sink in.  _ She was perfect.  _ She didn't know whether to believe him or not but she had no choice but to trust him. 

Sitting back, she tried to compose herself, straightening out her paperwork and releasing a slow breath. Maybe she'd regained some ranking in Dean's eyes because she stayed up for most of the night making these notes. Maybe she'd saved herself from punishment. She felt like she knew enough about all the rival mobs in the area, through her research she knew what made them tick; who hated who. Luckily enough, the Gala had a no violence policy. People laid down their arms before they entered and anyone who broke the rule, was permanently banned from future events. This gave any mob the perfect opportunity to build business and scope out their rivals. 

As she took in a deep breath, Y/N looked at herself in her dresser mirror. She tried to push the thought of The Master and where she went wrong to the back of her mind. Today was a new day, today was the day she was going to be the best version of what Dean wanted; she was going to make sure of it. 

-

As the clock struck two in the afternoon, Y/N descended the stairs in the main hall to approach the front doors, her heels clicking along the wood flooring. She knew Dean would be waiting for her outside, she’d been told so earlier on by Benny when he came by her room to pass on the message. She stood just behind the doors, her hand resting on the doorknob as she took a deep breath. She was nervous for the first time in a long time. She was nervous to be alone with Dean for the rest of the afternoon. The last time he had taken her out, she’d felt confident in her skills and what she was capable of. She was able to win Dean some business and in the process, she was able to feel his  _ incredible _ lips on hers. Then last night happened. The image of him being wrapped around another women infuriated her but she knew she had no right to feel that way. 

Taking a deep breath, she opened the door and her eyes immediately fell onto the green eyed Winchester who was leaning against a sleek black car, legs crossed as he spoke on the phone. He was still dressed in the white shirt and suit pants from earlier, only this time he was adorning the matching suit jacket. Closing the door behind her, she slowly made her way down the few front steps, catching Dean’s attention. As he looked up from the floor, his eyes caught hers and he offered Y/N a soft smile before wrapping up the phone call. 

“Wow,” Y/N gushed, her eyes landing on the smooth black metal Dean was leaning against, admiring the car for all its beauty, “a 1967 chevrolet impala. Is she yours?” she questioned as she came to Dean’s side, her hand sliding over the roof of the car. 

“You know your cars, sweetheart,” Dean praised, pushing off the car to face Y/N as he tapped the roof with his palm, “yeah, baby here is all mine.” He beamed as he looked down at Y/N as she walked around the car, admiring her for all she was worth.  

“Baby?” she questioned as she looked up at him from under her lashes, a little smile playing at her lips. 

“Oh yeah, wait until you hear her purr,” he continued as he opened the passenger door for her. Y/N tucked her hair behind her ear as she slid into the front seat, her eyes scanning the interior as she took in just how well the car was looked after. It looked like it hadn’t ever been used. It didn’t take long for Dean to slide in next to her from the opposite side, turning the keys in the ignition and letting his grin grow when he heard the familiar growl of the impala’s engine. 

“Wow. She sounds amazing, she's in really good condition, Dean,” Y/N told him as her hand smoothed over the leather around her. She didn’t see that Dean kept glancing over at her as he started the drive to their destination, a fond look in his eyes as he took in her reaction to his car. 

"Do you know much about them? Cars?" he asked, one hand on the steering wheel, the other on his lap as he stared out onto the road in front of him. 

"I had a client once that was all about vintage car auctions and he wanted to wow the fellow auctioneers. Ergo, I learned a thing or two," Y/N explained, leaning back into the seat to get comfortable as she rolled down her window to let in some fresh air, her hair blowing gently with the breeze.

"Well call me impressed," Dean flattered, glancing over at Y/N once more as they stopped in traffic, "she's my pride and joy. Thought I'd share her with you," he admitted, his voice low as he offered Y/N a warm smile, one that didn’t quite reach his eyes. 

"I… I appreciate that," she responded a little quieter than before. She held his gaze for a moment, her stomach turning over as she processed his words. He wanted to share something with her, something that means something personal to him. Dean was slowly surprising her and in turn, it made her want to learn more about him. She’d never been driven around by her client before, it was always chauffeurs or bodyguards so this was another first for her, one she was enjoying. 

When Y/N first met Dean, she thought he was an arrogant asshlole, the way he acted certainly gave her the means to do so.  However, slowly but surely, she felt like maybe Dean was showing his true colours. Maybe he wasn’t an arrogant asshole, maybe he was just a man who was trying his hardest to make his family business successful for those around him. Y/N knew as well as anyone to not judge a book by their covers as you never know what might have happened in someone's past to make them who the are. As she glanced over at Dean once more, watching how he drove the car along the asphalt with ease, his sleeves rolled back casually as his right hand rested on the steering wheel, she felt an odd sense of calm wash over her. He was starting to open up to her; she only wished that she could do the same in return. 

-

"Here we are," he announced as he pulled up at the edge of the sidewalk. Y/N frowned slightly at the quiet street, looking around and over her shoulder to see that there were little shops or passers by. But as she turned to look out of her passenger window, her eyes fell on the quaint boutique that was on the corner of the street. A bay window rested on either side of the door, both of them full with lavish ball gowns and elegant dresses laced with crystals. Y/N continued to stare in astonishment, not realising that Dean had gotten out of the car and was already opening her door for her. 

"Ellen is a genius seamstress, whatever you want, she can accomplish." Dean smiled down at Y/N as he held out his hand to help her out of the impala. Closing the car door, she matched Dean’s pace as he started walking towards the store which was a few feet away. It wasn’t long before they stood in front of the red wooden door. Dean took a hold of the handle and slowly opened it for Y/N, encouraging her to enter first, a little bell above them signalling their entrance. 

Y/N was in awe, as soon as she stepped inside she was surrounded with all different types of fabrics, gowns and jewels.  On one side, diamond tiaras and lavish necklaces were on display in glass cases where on the other side of the store stood all different types of materials and gowns. She’d seen many dress stores in her time but nothing like this. Even though it was so lavish and elegant, it also felt very personal. She didn’t have long to take in her surroundings as a middle age woman came bustling out the back at the sound of the doorbell. 

"Dean, honey, how are you?" she sang, rushing towards him with open arms as she engulfed him in a hug. As she pulled away, she brushed her brown hair out of her face, her hands automatically checking that the measuring tape dangling around her neck was still there. 

"I'm good Ellen, everything OK here with you and Bobby after…" Dean trailed off, making Y/N frown slightly. What had happened? His hand was on Ellen’s shoulder, his thumb brushing back and forth in a comforting manner as he awaited her answer. Ellen just patted his hand, giving him a small but reassuring smile. 

"Oh we're all fine, don't you worry about us. Instead how about you introduce me to this wonderful woman next to you?" Ellen gushed as she looked towards where Y/N was standing. Dean’s lips broke into a wide smile as he came to stand closer by her side. 

"This is Y/N, the main lady in my life," he introduced, his large hand reaching out to encase hers. It was a move that made Y/N’s breath hitch in her chest, it was a move that felt intimate and it had taken Y/N completely off guard. So when he interlaced his fingers with hers and brought their entwined fingers up to his lips to kiss softly, she had to keep reminding herself that this was all an act, no matter how weak in the knees she felt. 

"Well knock me down with a feather," muttered Ellen, her hand resting on her chest with shock at what she was seeing. "Well let's get started, sweetheart. I guess you're here for a dress for the Gala?" she questioned, coming around to slide an arm over her shoulder as she awaited her answer. Y/N just looked at Dean to which he nodded before he let go of her hand. 

"Yes, ma'am. I am indeed," Y/N replied politely, already missing the warmth of Dean’s hand as she looked back towards Ellen.

"Oh stop that formal stuff right now. It's Ellen to you, honey," she told you as she rubbed your shoulder softly. "Now what kind of thing did you have in mind?" she asked, an excitement in her eyes as she awaited Y/N’s decision on her dress. But Y/N had no idea where to even begin. She’d seen photos of the dresses other women have wore to the event but she didn’t know what to wear herself. Usually, that all came down to her client.

"Erm, Dean? What did you have in mind?" Y/N asked as she turned her head to look over her shoulder, waiting for his answer. As soon as the words left her lips, Dean’s eyes widened slightly as he tucked his hands in his pockets, slight confusion masking his features at her question. 

"Sweetheart, this is your rodeo. You can have whatever you want." He shrugged, a warm smile spreading across his lips before he found the slightly worn couch to the side of the store and sat himself down. Y/N took a deep breath, not being able to get used to controlling her own choices as she started to look around the store. Taking in the materials and premade gowns before her eyes landed back on Ellen’s. 

"I… I don't know. I'm sorry," Y/N apologised, a slight panicked look on her face as she began to play with her fingers.  

"Honey, don't be sorry. Let me show you some gowns and materials and then we can let our creative juices flow." Ellen rubbed at Y/N’s shoulders comfortingly before she guided her to sit on a separate much luxurious couch surrounded by materials, folders and samples for her to look at.  

Y/N felt a little overwhelmed with it all, normally a gown was chosen for her or she was taken to a store where one was picked to buy there and then. She never had the chance to  _ design _ her own. She decided to start with the basics, looking at gowns Ellen had made previously and letting her know what bits she liked from what dress as Ellen took notes. Once they’d gone through the dresses, it was time to move onto materials and colours. Y/N was spoilt for choice, running her hand over the different fabrics as she listened intently to Ellen’s advice. 

Every now and again, Y/N would look over her shoulder to ensure Dean was still there with her. Sure enough he was, either looking at his phone or looking directly at her which made her smile. Even though she was designing this dress for herself, she was also designing it for Dean. She wanted to look perfect for him. She wanted to look elegant yet desirable, she wanted Dean to see her how she wanted him to see her. 

Soon enough, Y/N had chosen her material and colour, deciding on little detailing on the dress as she preferred the plainer look. Ellen took a moment to piece it all together on her pad, sketching it out quickly using Y/N’s notes for reference. When she finished and turned the notebook over, Y/N couldn’t hold back the grin, she was excited to see it come to life. She’d chosen a pale blue in colour, the bodice was fitted with a sweetheart neckline that had a small V cut out between the breasts, loose straps made from lace would drape around the tops of her arms. From just below the hips, the material became a lot lighter, bundled together to allow it to flow and move easily. Y/N wanted floor length with just a bit of a train, nothing too excessive and she also added a slit to mid thigh on her right leg.

She offered her help to Ellen as she gathered everything together to get started but she was having none of it, telling Y/N to sit and relax and enjoy this moment. Ellen hustled off into the back before bringing out a tray filled with champagne, fresh orange juice and an array of fruits to nibble on. Y/N was shocked but grateful as she placed the tray down in front of her. She once again turned to Dean and noticed he had a mug of coffee in his hand before he looked up and winked at her. She let her hand hover near one of the flutes of champagne, biting at her bottom lip as she thought about drinking one. But, wanting a clear head around Dean, she opted for a glass of fresh orange instead. 

A couple of hours later, Y/N was stood on a large circle pedestal in front of three tall floor length mirrors. She was wrapped in the material she had chosen, the outfit pinned together as Ellen worked on adjustments, ensuring the dress was going to be the perfect fit for her. However, a sudden boom of a gruff voice made Y/N jump.

“Dean! It’s good to see you, son,” the voice called and Y/N looked over her shoulder to see an elder man in a tattered looking cap, jeans and flannel walk over to him.

“Hey, Bobby,” Dean replied with a smile, standing to give Bobby a quick hug in greeting before they started to chatter between themselves, Bobby turning to look at Y/N as Dean smiled and she felt a wave of nerves wash over her at the thought of Dean talking about her. 

“That’s Bobby, my husband. He can be a bit of an old grump but I wouldn’t have him any other way,” Ellen told her, making Y/N turn back around and look down at the woman that was bunching some material together at her feet. 

“Does he work here too?” Y/N asked quietly, tucking some hair behind her ear as she continued to watch Ellen work. 

“Are you kidding, honey?” Ellen laughed, stopping to look up with her as she continued to chuckle at the thought.“No, Bobby owns the garage further on down the street, sorts out all the vehicles for the boys when they need him too. He and Dean make quite the team when it comes to restoring cars,” she informed Y/N and it made her smile. Something about the thought of him being hands on made her quiver, the thought of Dean covered in oil and grease made her groan inaudibly. 

“There, what do we think?” Ellen asked, as she finalised the last pin in place a few moments later, breaking Y/N out of her fantasy filled thoughts. When she looked at herself in the mirror, she gasped. The dress had turned out even more wonderful than she had ever imagined, it was worth the amount of hours she had been standing there. All that was left to do was for Ellen to stitch it all together properly. 

“Ellen, it’s...it’s beautiful,” Y/N whispered, her eyes pricking with happy tears as she continued to take in her reflection, her hands coming to the light material that hung from her waist, swishing it from side to side. However, even though she loved it, she needed to ensure that her client loved it too. “Dean?” she questioned, her heart beating a million miles a minute as she waited so desperately for his approval. She hoped she’d got this right. Dean turned to looked up from his phone at the sound of her voice, his lips instantly parting at the sight of her as he stood, taking his time to walk over to her. 

“Sweetheart,” he breathed, his green eyes roaming up and down your figure slowly, drinking her all in, “you look,” he continued, before a tiny frown appeared on his brow, his words lost. His eyes scanned the glass cabinets that were behind him, his fingers ghosting the glass until he found the item he was looking for. 

“Turn around,” he instructed softly and Y/N did as she was told, watching him through the mirror as he approached her. He stepped onto the platform, his body a finger length away from hers as he circled his arms around her neck. She watched as he pulled a string of diamonds from his palm, allowing them to fall elegantly over her chest as she watched him intently. She automatically lifted her hair from her neck, allowing Dean to fasten the clasp of the necklace with ease. She felt how his fingers brushed over her skin as his hands encouraged her to drop her hair, his palm now resting flat on the bottom of her back as he looked at her fondly through the mirror. 

“You look beautiful,” he husked, a warm smile on his lips as he held her gaze for a moment. Y/N felt like she had to concentrate on every breath she was taking else she might forget to breathe. The way he was looking at her made her feel like she was the most wonderful being on this planet. In that moment, her heart beating hard against her ribs whilst her stomach turned over with nerves, she had forgotten everything. For that moment, she felt happy. 

However, the sound of someone clearing their throat encouraged them both to break their stare as they turned to look at Ellen, a big beaming smile on her lips as she looked at her finished product. She walked behind Y/N, patting Dean on the chest gently before coming to rest her hands on Y/N’s shoulders. 

“Give me a day to get it all stitched together and i’ll drop it by the manor,” Ellen told you. “We’ll leave you to get dressed,” she continued and all you could do was nod as your cheeks ached from your smiling. It took a few moments for you to carefully get out of the material you were wrapped in without pricking yourself on any of the pins or ruining the placement of them. As Y/N stood in her underwear behind the floral dressing screen, she watched through the open slit at the top as Dean and Ellen stood talking before he handed over a very large sum of money. He gave her a hug and kissed the top of her head before they continued their conversation. The money hadn’t surprised Y/N; due to her lifestyle she was used to seeing wads of cash here and there. It was how he acted around his family; her first impressions of him were completely wrong. 

As she continued to dress herself, Y/N mind wandered back to how Dean’s fingers danced over her skin, how his breath fanned over her ear as he told her she looked beautiful and she couldn’t help the arousal she was feeling. She took another opportunity to glance over at him through the gap and her cheeks flushed when she saw he was staring back at her, his lips pursed slightly and his arms folded. He looked delectable and she wished she was here with him under other circumstances. 

-

After a long goodbye with Ellen, Dean had placed his hand on the bottom of Y/N’s back as he guided her to the passenger side of the impala. She felt like she was fit to burst; all of her frantic feelings from the morning had vanished.  As Dean unlocked his car and held the door open for her, she looked fondly at the Winchester as her hands rested on top of the door frame.

“The dress is going to be so beautiful, Dean, I’m not going to want to give it back,” she told him honestly, her smile still wide and her cheeks still aching. Dean looked down at her, a small crease on his brow and he mirrored her smile. 

“Who said anything about giving it back?” he retorted, letting a little laugh bleed from his lips as he brought his hand up to tuck a stray piece of her hair behind her ear.  “Sweetheart, that dress is yours to keep,” he told her honestly.

“Really?” Y/N gushed, her eyes suddenly wide and her smile, if possible, was widening even more. Dean just let out a low chuckle at her excitement.

“Really, even the necklace that went with it.” He tucked his hands into his pockets as he watched how her smile faded slightly, her face relaxing as her eyes stayed wide. She slowly sunk into the passenger seat, her feet still on the pavement as she played with her hands. He’d bought her the diamonds too? Just how much was she costing him? She suddenly felt guilty that she wasn’t doing a good enough job to get all this special treatment; that she didn’t  _ deserve _ this treatment.

“Dean, I’m not-” she started, her guilt starting to bubble inside her as she forced back some tears, not wanting them to be visible to Dean. But unbeknownst to her, he’d noticed the shift in her body language and he’d come around to stoop at her feet, using his finger to lift her chin to look at him. 

“Not what? Worth it?” he husked, his green eyes boring into hers, “Y/N the way your face lit up when you looked in that mirror, all dressed up, was worth the amount of money I paid. If not more,” he told her softly, his hands coming down to rest on his knees. “Come on, let’s go get something to eat,” he offered, suddenly changing the topic and taking the moment with him as he stood up, moving to shut the passenger door.  

“I...I…” she stuttered, not knowing what to say or how to even reply to what Dean had just said. Instead, she just tucked her feet into the footwell of the car as she looked back up towards the man that was slowly changing her life.

“Y/N you’ve had about 4 strawberries since yesterday morning. It’s now after eight and you need some food in you. Luckily, i’ve got the perfect place in mind,” he told her, a grin on his lips as he gently shut the door and walked around to the drivers side. 

Y/N didn’t even register that Dean had got in next to her or that he’d started the engine, her mind was just replaying the words he had spoken over and over again.  

_ She was worth it.  _

**Notes for the Chapter:**

> Thanks so much for reading! I hope you enjoyed chapter 12! Ahaha i hope this has redeemed Dean for some of you… ;)
> 
> I can't wait to share the next few chapters.


	15. Chapter Thirteen

The sound of the impala’s engine and the low hum of his classic rock tape was all that could be heard as Dean drove along the highway. He looked over at Y/N, her hair slowly flowing behind her as the nights breeze came through her open window. He couldn’t get the image of her in that dress out of his mind. Even though it was nowhere near complete, and that were bits of excess material here and there, she still looked breathtaking. He remembered the look on her face when he introduced her to Ellen as the lady in his life, he hadn’t even thought about it, the words just bled from his lips like it was normal. Even when Bobby came and saw him, he’d told him the exact same thing. He allowed his smile to widen slightly when he remembered what Bobby had said to him.

_“You lucky son of a bitch.”_

He was lucky; he agreed wholeheartedly. Even if this relationship was a lie, he was lucky enough to have this woman working with him to rebuild his empire. He was lucky enough to have a woman smart enough to be able to take on his rivals. He was lucky enough to just be in her company.

He rubbed at his brow as he turned off the highway, cruising down a street he knew all too well as he tried to figure out what was going on in his own head. Y/N had been silent the whole ride, he’d asked a few times if she was ok and she assured him she was; that she was just enjoying his music. That was like another brownie point to him as none of the other women he’d been with have ever shared his love for classic rock. But he couldn’t get out of his head the way she looked at him, with worry behind her eyes when she implied to him that she wasn’t good enough. His heart broke that she even thought that and it was making him question just what the hell was going on back at The Hemlock. The way she acted when he said he was going to report how well she was doing, fumbling and dropping her papers like he'd just told her some bad news. Then there was the way she shut herself off when she thought she’d stepped out of line. Alarm bells started to ring in his head and he just knew he had to get to the bottom of it, starting with breaking down a few of Y/N’s walls. 

Dean pulled up outside of a pizzeria, a few tables were littered outside with candles in jars, basking in the glow of the neon sign. He pulled the keys out of his ignition and noticed how Y/N’s eyes widened at the sight of it all. 

“Pam’s Pizzeria?” she asked, her voice timid as she looked over at Dean. “But...I...do they just do pizza?” she stumbled over her words as she waited for his answer. 

“Well...yeah. But it’s the best damn pizza you’ll ever have,” he breathed.“So believe me, whatever your favourite pizza is, Pam’s version will blow it out the water,” he promised as he opened his car door, his stomach rumbling at the smell of fresh dough. However he noticed that Y/N hadn't mirrored his actions and was still sat in the passenger seat. He leaned down to look at her, his arm resting on the roof of his car, his other keeping the door ajar. “You alright, sweetheart?” 

“Yeah, course." Y/N nodded, fumbling to grab hold of the door handle before she exited the impala. She smoothed down her outfit before walking to join Dean's side. He watched how she kept glancing around, looking over each of her shoulders as if she was expecting someone to be watching her. It had him concerned, his mind starting to reel off the possibilities of why she was so on edge. Was she in trouble? Was she working with someone to get information on his family? He couldn’t let the latter happen again; he needed to be careful. 

He reached the door to the pizzeria and pulled it open, holding it ajar for Y/N to pass through before he took one quick look around the car park to see if he could spot anything or anyone. Deciding to let it go for now, he took a deep breath before turning around and heading into the pizzeria himself, placing his hand on the bottom of Y/N’s back as he guided her to the counter. He noticed how tense she was, how her arms were folded across her chest and how her back was rigid; something was off. 

“Ahh if it isn’t my most handsome customer,” a female voice sounded and Dean looked up to see the owner, Pam, leaning on the counter,  “and his lady friend, what can I get you?” she sang, smiling at them both before her eyes settled on Dean. He smiled back at her, his hand clasping around Y/N’s hip tightly as he briefly scanned the menu.

“I’ll have a double pepperoni, stuffed cheese crust and Y/N here will have…” he looked down at her, leaving his question open hoping that she’d answer but instead he found her hands twisting together, her eyes looking between the menu, Pam and Dean before going back to the floor. 

“I...I don’t know. I’m sorry, I-” she stuttered, her hands coming to tuck the free hair behind her ears as she continued to look down at the floor. Dean frowned slightly, knitting his eyebrows together. 

“Give us a sec?” he asked Pam and she nodded as Dean gently pulled Y/N over to the side, away from prying eyes and ears. He was worried about her behavior, he was trying to not let his head rule his actions and jump to conclusions but he had to know the reason why she was acting so strange. He had to work this out. “Y/N, do you not like pizza? We can go somewhere else if you’d like? There’s this amazing burger place a few blocks over,” he offered, throwing his thumb over his shoulder.

“No...no it’s fine,” she immediately answered, her hands out palm flat in front of him as if to stop him from doing something rash, which only added to his confusion. He watched how she took a deep breath, her fingers picking at the edges of her nails as she looked at anything but him. “Look, it’s embarrassing ok? I’ve never...I don’t-”

“...have you never had pizza before?” He saw how a blush crept onto her cheeks and it was like something clicked in his head. How hesitant she was to enter the building, how nervous she was standing in front of the counter. _She’s never had pizza before._ It still didn’t explain why she was looking over her shoulder but he could always question that later. 

“N-no,” she answered quietly, as if she almost didn't want to admit it out loud. Dean’s heart went out to her and he allowed a small smile to grace his lips. He wasn’t going to question the why or how she’d never tried it, instead he was just glad he was going to share this first with her. 

“Well then, sweetheart, let me introduce you to the wonderful world of pizza pie. I mean, they aren’t burgers but they’re still pretty damn good. Let’s ease you in,” he encouraged, sliding his hand around her shoulder as he guided her back towards the counter where Pam was still patiently waiting. “One pepperoni, one four cheese, a beer and…”

“Just water please,” Y/N asked politely, her body language a little more loose than it was before. Pam smiled at them both as she wrote down their order.

“Coming right up. Your usual spot is free,” she told Dean, using her pencil to point towards the back where his table was. Dean just nodded his head in thanks before he guided Y/N around past the counter. He pulled back a black curtain that was just beyond the kitchen which revealed a private booth. It was in a half circle style, the leather seats were a deep red while the table was black marble. There were a few candle style lights hanging from the walls which added to the ambience. He watched on as Y/N studied the room closely, her eyes falling over the art that hung on the walls. It was a very different atmosphere to what she had experienced just a few metres away. 

Truth was, this was Dean’s private booth. He’d had a hand in helping Pam get started with her business after her last one began to struggle. He wanted his own space and to be away from prying eyes whenever he wanted some food, much like today. He slid into the booth and moved over so he was sitting at the back, center of the half circle before patting the leather next to him, encouraging Y/N to sit down. She did as she was told, slowly moving along the leather so she was sitting closer to him, much to his approval. 

“Thank you, again, for today,” Y/N told him quietly, her Y/E/C eyes boring into his. He smiled, his hand coming up to rub his slightly stubbled chin.

“Don’t need to thank me, Y/N,” he answered, his voice low. It surprised him how much she actually thanked him for doing things that, to him, seemed like a perfectly normal thing to do. It made him wonder what her other clients must have been like. His thoughts were broken when a waitress came in with their drinks in hand and placed them on the table without a word. His instantly wrapped his hand around his bottle of beer, pulling it towards his lips to take a generous mouthful. 

“Can I ask you something?” Y/N asked causing Dean’s green eyes to glance her way. He just nodded, placing his beer back down onto the table. “What had happened to Ellen and Bobby? Are they going to be ok?” Y/N’s words were hushed, her body leaning closer to him. He just looked up at her from under his brow, his head tilting slightly at her question which made her retreat back into the leather. “Sorry, I don’t mean to speak out of place,” she apologised.

“It’s fine, sweetheart,” he reassured her as she shuffled in his seat. He brought both hands to his beer bottle, wrapping his fingers around the glass before he started to explain. “A couple of weeks ago, they’re businesses got trashed. Ellen’s boutique and Bobby’s garage. We got there just in time to see some dicks light a few molotovs and throw them. Luckily, we got the fire out before much damage was done.” He looked over to see that Y/N had a hand in front of her mouth, her eyes wide with shock.  

“Shit, Dean. Do you know who was responsible?” she asked, placing her hand on his wrist with concern. He tried hard not to focus too much on the feeling of her skin on his, the way her delicate fingers were resting against him. 

“Not yet, but I’ll find out,” he responded, determination lacing his tone, “and when I do, they best start fuckin’ running,” he threatened, spitting venom as he spoke. He took another long drink from his beer, allowing the beverage to calm him slightly before he got too worked up. Ellen and Bobby were family, blood or not, and he would do _anything_ to protect family. After a moment of silence, he looked over to Y/N to see her staring at him, her eyes glistening in the dim light. 

“I could help find them, look over any news articles or files you have?” she offered as her small hand wrapped around her glass of water,  “I’m no Sherlock Holmes but I might be able to see something you might have missed,” she suggested, taking a small sip of her drink. Dean allowed himself to smile once more; contract or not, Y/N was going above and beyond for him and his family and he couldn’t be more grateful. Which was why he didn’t want her in the direct line of fire. 

“Sweetheart, that’s real nice of you but leave it to me ok?” he instructed. He watched as Y/N pulled herself away from him a little bit, nodding her head in acceptance. He sighed inaudibly. “Some of these mobs have crawled out of the very depths of hell. What they’ve done to women, taking what they want when they want, the states I’ve seen them in...Y/N I wouldn’t wish that on anyone,” he spoke softly, placing his large hand over hers on her lap as he implored her to look at him. Once she did, and she smiled, he felt his stomach turn over with nerves, a feeling that had been lost on him for a long time. He just hoped she understood where he was coming from. The sound of the curtain being pulled back alerted Dean and he removed his hand from hers just as Pam arrived at the table, tray in hand.

“One pepperoni, one four cheese and a side of complementary fries,” she sang, sliding the plates across the table before adding cutlery wrapped in napkins next to them. “Enjoy.”

“Thanks, Pam.” Dean felt his stomach rumble as he looked down at the cheesy meaty goodness on his plate. 

It had been hours since he’d eaten so the sight in front of him made him salivate. He didn’t need the cutlery Pam had provided, he never did. In his mind, pizza was a finger food and it would always remain that way. He slid the plate closer to him, his eyes scanning for the biggest piece before he pulled a slice away, the melted cheese stretching from the base. As soon as he bit into the slice, he felt his eyes rolls and an involuntary moan leave his lips. He was hungrier than he thought he was. A few mouthfuls into his slice, he looked over to see Y/N was still staring at her plate, her pizza untouched as she twisted her hands in her lap once again. 

“Are you alright?” he asked concerned, placing the crust of his pizza back on his plate. 

“Mm? Oh yeah, fine,” she flustered, bringing her glass of water to her lips. Dean narrowed his eyes slightly as he watched her drink, wiping his mouth on a napkin. He was curious about her behavior, he was still suspicious of her actions from earlier so he thought now was the time to get to the bottom of it. 

“So tell me something, how come you’ve never had pizza before? You telling me after you got wasted in college you never rolled down to your local pizza place for hangover food?” he asked, prying coyly for information as he picked at a couple of fries from the plate between them. He saw how she frowned slightly before placing her drink back onto the table. 

“I didn’t live in the dorms, I-I was at home, so food was always available,” she explained with a slight shrug of her shoulders. 

“Okay,” Dean drawled, “so you’ve never had any late night sleepovers with the girls at work, all sitting around in your underwear exchanging dirty stories and eating junk food?” He asked her with a slight wiggle of his eyebrows and Y/N could only roll her eyes playfully.

“I think that only happens in your head,” she giggled. “They-I just like to eat healthy,” she quickly corrected herself, letting out a long sigh. Dean knew he wasn’t hearing things, she had definitely said _they._ Was someone controlling what she ate? Parents, family or even her employer? He needed to make her feel more at ease, he needed her to know that she was safe with him and that she could eat whatever she wanted whilst she was in his company..

“It’s just us, Y/N, I won’t tell if you don’t,” he told her softly, placing his hand over hers comfortingly as he looked into her eyes. “We’ve all got to treat ourselves sometimes,” he continued, giving her hand a gentle squeeze before pulling away and going back to his own plate. 

There was a long pause between them. Dean didn’t want to pressure her anymore so he picked up a handful of fries and continued to eat. He told himself that if after a few moments more she still hadn’t eaten, he’d take her home and have Magda make her whatever she wanted. But he wouldn’t have to. Y/N smoothed her hands down her dress, shuffling herself closer to the table and a little more to Dean before she looked back up at him, her fingers inches away from the plate.

“So, you just pick it up?” she asked, watching as Dean himself picked up another slice of his pizza. All he did was nod before taking a big bite out of his food.

“Let loose, baby,” he grinned, his cheeks full of the italian treat. She clenched her fingers a few times, mouthing the word ‘ok’ before she slid her finger gracefully under the crust. Dean didn’t want to stare but he couldn’t help but be marvelled by the change in her already. Her eyes were sparkling, her lips were curling into a smile; he enjoyed seeing this side of her. She was hesitant as she picked the slice up, turning it around so the pointed end was facing her lips. She took one more deep breath and slowly but surely she took her bite. He saw her eyes widen before they fluttered closed, her body sinking into the seat.

“Oh my god,” she moaned, her hand coming up to cover her mouth. “Oh my god, Dean!” she moaned once again and he couldn’t help but bite the corner of his lip. The sounds she was making was sending his imagination wild. He knew he shouldn’t be thinking this way when she was innocently eating pizza, but he couldn’t help but imagine her making similar moans if she were under him. 

“Good, huh?” Dean cleared his throat, shuffling in his seat slightly as he placed his half eaten slice back on the plate. All she could do was nod before she took another generous mouthful which caused Dean to laugh slightly. He reached for his beer, his fingers tracing along the neck of the bottle as he watched Y/N reach for a napkin. 

“This is amazing,” she praised, wiping her mouth gently on the disposable tissue before reaching for her next slice. Dean could only smile widely at her, glad that she had enjoyed her day with him. He hoped that this had made up for his actions, he hoped that maybe she would see him as not some pussy hungry asshole but as someone who had plans for his future, someone who was serious about his family business. 

As he drank some of his beer, he made a mental note to talk to Charlie about the information he’d figured out from Y/N. That she stayed at home whilst she was at college, that maybe someone was controlling her diet. It wasn’t much to go on but it was something and sometimes, even the tiniest of something can open up a whole new avenue to explore. He was determined to find out who the real Y/N Y/L/N was. 

After a couple of slices,  Y/N had mentioned that she was full as she rubbed a hand over her stomach. Dean didn’t protest, feeling pretty stuffed himself, he flagged down a waitress and asked for them to put the remainder of their food into a box so they could take it home. He had been trying for a while to convince Y/N that day old pizza tasted amazing and was one of the best breakfast foods but she was not convinced. Leaving Dean to tell her _don’t knock it ‘till you try it._

With the pizza box in one hand, Dean led Y/N out of the pizzeria and back to his car, making small talk along the way. He was happy to see a difference in her, she looked lighter somehow, as if a weight that had been holding her down had been lifted and he was thankful that he was able to do that for her, at least for today. Like a gentlemen, he held open the impala’s passenger door for her, sliding the pizza onto the back seat before taking his position on the drivers side. As he started the engine, Y/N shivered slightly and rubbed at her arms. Without hesitation, he peeled off his suit jacket and handed it over to her. At first she refused, stating she was ok but eventually she gave in and snuggled herself under the material as Dean pulled away from the pizzeria.  

The drive back to the manor was a quiet one, the sound of Dean’s music was the only thing that filled the impala, that and the gentle hum of the engine. Dean didn’t mind though, it was a comfortable silence and as he looked over to Y/N sitting next to him, he was happy to see that she looked content curled up in his clothing. She’d moved from having the jacket resting over her to actually wearing it, wrapping the material around her frame to keep her warm. 

As Dean pulled up in front of the manors front doors, he was reluctant to say goodnight to her so soon. Even though he’d spent the better part of the day with her, he didn’t want it to be over. He pulled the keys out of the ignition slowly, exiting the vehicle and moving around to open her door for her. He helped her out of the car and he smiled when she wrapped his jacket even tighter around her frame. He placed his hands in his pockets as they both walked up the front steps, side by side before entering the manor. He knew this was where they would part ways for the evening, unless...

“Fancy a nightcap?” he offered, rocking on his feet slightly in the hopes she’d agree. 

“Sure,” he nodded, a small smile pulling at her lips which made Dean sing internally. The night was not yet over. 

He escorted her to his office, where he kept his good whiskey, undoing the top few buttons of his shirt as he did so. He opened the door, allowing Y/N to enter first before closing it behind them. He reached out for the light switches to his left, allowing just a dim light to glow throughout the room as he made his way over to his drinks cabinet. He noticed out of the corner of his eye how Y/N was slowly walking around his office, studying the books on the shelves or the photos resting on tables. It was only when she came to a shelf above the fireplace that she stopped. Dean unscrewed the bottle of alcohol, pouring each of them a generous helping before pinching the glasses together with one hand, holding the bottle of whiskey with another. 

As he turned around, he noticed that Y/N was staring at a picture of his parents, the frame in her hand as she studied it. He gently placed the bottle onto the coffee table that rested by the couch before joining Y/N at her side. 

“Your parents look really happy here,” she spoke softly, placing the photo frame back on his mantle. Dean just gave her a weak smile as he held out her tumbler of whiskey to her, his eyes landing on the photo too. 

“They were. It was Dad’s birthday, just before his party started,” he explained, a small laugh leaving his nose as he reminisced. “You wouldn’t know that five minutes before that was taken, Mom was giving him hell for not taking her to his latest deal,” he told her fondly, the memories of his Mom was filling his heart with warmth. He turned around, walking over to the couch to sit himself down. “Dad liked to think he was the don, but we all know the true don was her.” He leaned his head back against the couch cushion, both hands encasing his drink as he stared up towards the ceiling, memories of his parents flooding his mind.  

“What happened? With the assassination?” Y/N asked softly, the dip he felt in the couch indicating that she had come to sit next to him. Dean slowly raised his head and looked down at his whiskey, his thumbs tapping against the glass. “Sorry, I shouldn’t have asked,” she apologised, her hand coming to rest on his shoulder.  

“It’s alright, sweetheart. Just not spoken about it in a long time,” he whispered, his voice low. He looked over to his right to see that Y/N had curled onto the couch next to him, her knees angled at him, her hand that was on his shoulder was now resting in her hair as she waited for his story. Dean took a deep breath and a sip of his whiskey. “They were driving to a mini vacation. Mom had been on about a break in the mountains for a while so Dad surprised her. As they were coming around the pass, they got ambushed. Two clean headshots. Whoever was behind it then tried to cover their tracks by pushing the car off the pass, but it was found by a ranger.” As soon as Dean finished his sentence, he downed his drink in one, hissing when he felt the burn in his throat. He reached forward to the coffee table, reaching for the whiskey bottle to top up his glass.

“Dean...I…” Y/N started, the tone of her voice said it all; the shock she was feeling. Dean just shook his head, cutting her off. This conversation was opening a wound that he thought had healed a while ago. 

“We didn’t want the cause of death in the papers so Sammy did some damage control. We searched for ages trying to find the fucker that was behind it but every lead led us to a dead end. So I lost myself in whiskey and women, buried my head in the sand which left our mob to go to shit,” he confessed, his voice husky as he swallowed the lump in his throat. He hated himself for a long time. At the start, just after his parents' death, he threw himself straight into the business. He was sorting out contracts, deals and so forth; he didn’t allow himself to grieve. He couldn’t even remember when it all became too much, he couldn’t remember the day he snapped and started getting blind drunk every day. He couldn’t remember why he decided to lose himself in women. He just knew that he did it so he would feel something other that the pain he was experiencing. 

“It’s not shit Dean. So you lost your path, we all get lost sometimes but we can always make it back home, with the right help,” Y/N softly encouraged, her free hand coming down to comfort him, her thumb caressing his cheek. Dean subconsciously nuzzled into her palm, her touch was gentle yet electrifying. He looked up to see her Y/E/C eyes staring into his as she moved closer to him, her head inches away from his. 

“You think so?” he whispered, his eyes dropping from hers to stare at her plump red lips. His heart was beating hard in his chest and he was so desperately hoping she couldn’t hear it. He couldn’t help but allow himself to inch that tiny bit closer, his nose ghosting over hers. 

“I do,” she breathed, her breath fanning across his cheeks. Dean took a slow deep breath as he closed the remaining distance between them, his perfect lips encasing hers. He removed one hand from his whiskey to come and caress the side of her face, his calloused thumb resting against her cheekbone as his fingers cupped the back of her neck.  

He never wanted to let her go.

**Notes for the Chapter:**

> Thanks for reading guys! Hope you enjoyed this one!
> 
> Sorry it took longer than usual, kinda been feeling a little on the low side these past few days so inspo was at an all time low. But hey ho! 
> 
> Thanks for reading!


	16. Chapter Fourteen

**Notes for the Chapter:**

> Oh my goodness!
> 
> First of all - I'm so so so so sorry about the delay. Being honest, this chapter was ready to go on Thursday - posted it to tumblr and completely forgot to post it here - until now *facepalm*
> 
> Second of all - I'm sorry again it's taken so long to update this fiction. I've had a lot of stuff happen in my personal life that's made it a little bit shit. But - that's all done with now and thanks to some amazing people on tumblr and in my life, i've picked myself up and here we are - unofficial hiatus is over lmao!
> 
> I've planned this fiction out to the last letter - it's gonna be thirty chapters so we're just about halfway there ;) 
> 
> Hold onto your hats!
> 
> Thanks for sticking with me, i hope you enjoy!
> 
> -Winchest09 xox

Y/N stared into the floor length mirror in front of her as she smoothed her hands down the material of her dress. She still couldn’t believe how beautiful she felt; she still couldn’t believe that it was specifically made for her. Ellen had dropped by earlier to bring the dress and to help Y/N into it, ensuring it fitted perfectly after the final adjustments had been made. She couldn’t thank Ellen enough for everything that she’d done, feeling truly humbled by the fuss that was being made for her; she just hoped that Dean would still approve of her look. 

It had been just under a week since she and Dean had kissed in his office. A kiss that was short lived thanks to Sam walking into the office unannounced. He apologised for the intrusion, clearing his throat before asking to speak to his brother in private. Of course, Y/N complied and quickly made her way to the rooms exit, sneaking a glance back at Dean over her shoulder to see his green eyes lingering on her. She couldn’t help but bite back a smile as she left the room, hastily making her way to her bedroom alone, her fingers touching her tingling lips the whole way. 

The days that followed had been spent researching and learning everything there was to know about anyone who was of importance attending the Gala. Dean had spent the majority of his days in the boardroom, held up in meetings or going out on jobs with his brother. In truth, she’d hardly seen him and she was beginning to miss his company. He’d sent her notes here and there, checked in with her over the phone or sent her a dazzling smile if they happened to cross each other’s paths but she’d been left to her own devices more often than not. So tonight was a night that she was certainly looking forward to. Tonight was the night of the Gala and she couldn’t wait to be the girl on his arm. 

Taking a deep breath, Y/N gave herself a few words of encouragement. Even though she was excited to be spending time with Dean, she had to remember that she was only here on a job. She had to make sure that she brought her A game to this event, she had to help Dean win back business for the Winchesters. She couldn’t let him down; she couldn’t let The Master down. She let her eyes shut momentarily at the thought of what would befall her if she failed, if she did let Dean down and it got back to The Hemlock. Her life wouldn’t be worth living. 

Y/N brought her lipstick to her lips, slowly painting the skin a subtle red colour. The words that Dean had mentioned a few nights before, swimming around her mind.  _What they’ve done to women, taking what they want when they want, the states I’ve seen them in…Y/N I wouldn’t wish that on anyone._  If only he knew where she had come from and where she was chained to. If only he knew about the training Alastair put his girls through, the years of torment, the years of childhood that were lost. But he would never know, there was no escape for her and she knew that. Instead, Y/N decided to enjoy the free reign that she had whilst being with her client, for it was the only freedom she would ever have. 

As she pressed her lips together, the sound of three gentle knocks upon her door made her stomach flutter. With one final look in the mirror, she took a deep breath and waited for Dean to walk in like he always does. When she noticed the door handle dip, her stomach fluttered as she held her breath. Her eyes were cast down slightly, the sight of his black leather brogues coming into her view as she slowly raised her eyes to look at him from under her lashes. There he stood, stunningly handsome in his black suit, his black tie knotted perfectly around his neck which contrasted beautifully against his white shirt. When her Y/E/C eyes met his dazzling green orbs, she couldn’t help but feel her red painted lips curl into a nervous smile. Dean’s eyes slowly scanned her figure, visually taken aback by how she looked. He had one hand resting in his pocket as the other one gestured towards her, his palm turned upwards as he struggled to string a sentence together. 

“Wow, Y/N…wow,” Dean breathed, slowly walking towards her, “You look…you look,” he struggled with his words which made Y/N hold her breath and bow her head to look at the floor, “you look beautiful,” he finished, his hand coming up to tuck under her chin, lifting her face ever so slightly so she could look into his eyes. It was an action that made her blush, her fingers lacing together in front of her as she let his approval wash over her. 

“Thank you,” she replied, her words quiet as she lost herself in the sea of his emerald eyes, “I must say you look quite handsome too,” she complimented, a small smile gracing her lips. Dean didn’t respond. Instead, he walked slowly behind her, his finger tracing its way over her shoulder to the back of her neck where he brushed some of her hair aside. It was in this intoxicating moment, where his cologne washed over her like a wave of calm that she felt the coolness of metal grace her chest. The diamond necklace that he bought for her was now elegantly resting against her skin, glistening in the light. Her hand came up to touch the stones, reminding herself that he bought it just for her before she felt his hand on her forearm, turning her to face him. 

“Perfect,” he husked, “you look perfect.” He held her gaze for a second or two and in that moment, she contemplated closing that small gap between them, kissing his lips for a third time. But instead, she settled with placing her palm flat on his chest, fixing his tie a little before looking up at him from under her lashes. 

“Let’s go and show these people who the real don is around here, hmm?” she encouraged, her voice resonating through Dean like a purr. He nodded, his smile widening into a grin as he took her hand and led her out of her bedroom and down towards the front of the house. 

-

As she walked down the front steps from the foyer, she smiled at Sam who was already sat waiting in the front of the familiar armoured black Range Rover, the back door left open for their entry. Garth stood obediently next to the back passenger seats, his hand resting on the door handle as he nodded his polite greeting to Y/N and Dean. She grinned back at him, nodding her head graciously before bending to pick up the front of her dress with her free hand, Dean standing behind her to help her slide across the seat. Sam immediately turned in his place and offered his hand to help, an offer that she took. 

“You look amazing, Y/N,” Sam complimented as she let go of his hand, leaning into her seat to get herself settled, Dean shutting her door for her. 

“Thank you, Sam,” she spoke softly, her hands resting in her lap as Dean opened the door on her left.

“I’m a lucky son of a bitch, that’s for sure,” he beamed, taking one of her hands in his as soon as he got himself settled into the back of the Range Rover. 

“You ready?” Sam asks, his dark eyes glancing up at them through the rear view mirror, although his gaze seemed to be resting more on Y/N which made her nod her head enthusiastically. 

“I got this,” she assured Sam and he nodded, his gaze now focused on the road ahead of them as Garth started to pull out of the drive. Dean squeezed her hand slightly for reassurance and she allowed her nerves to simmer slightly. Just knowing that he had the confidence in her to do her job was the small boost she needed to have faith in herself.

The drive to the Gala took a little over thirty minutes, nothing but the hum of the radio and idle chit chat between the boys ensued whilst Y/N watched the world go by through the window. It was only when Dean squeeze her hand twice gently did she turn to look at him. He nodded towards the front of the car, a silent instruction for her to look that way and when she did as she was told, she gasped at what she saw. Garth had pulled into the long mile stretch of road that led up to the mansion, strings of lights decorated the trees that lined driveway and as they got closer to the courtyard, Y/N noticed the large circular fountain as the centrepiece. 

As the car circled around to join those other vehicles waiting in line, Y/N observed the people that were already making their way into the building. She took note of how they were dressed, how they acted and presented themselves. As she studied everything around her, she was unaware that the Winchester brothers had already left the vehicle, Dean making his way around to her to open her door. The movement made her jump slightly, bringing her mind back to the company she was sharing her evening with. Dean stood there, one hand resting on the black metal, the other held out for her to take. Sam was stood just behind him, fixing his tie before he placed his hands in his pockets as he watched Y/N exit the car. He gave her a warm, reassuring smile as she came to stand in the middle of the two men. Dean’s hand left hers but the contact was only cut for a second as his hand came to softly rest at the bottom of her back, the warmth of his palm radiating through her. With that move, he began to lead her to the tall open doors of the building, guards on either side scanning guests as they entered. Random weapons being taken off the odd guest in line; mainly knives and guns which were disposed of in a box where another guard kept watch. Y/N took a deep breath as she picked up the front of her dress to ascend the stairs. This was it, this was showtime.

She was escorted through the grand foyer, crystal chandeliers that hung from the ceiling emitted a warm glow over the crowd. As Y/N glanced around, she saw how every woman there was shimmering with diamonds, the light making them twinkle as she walked past. The men were all dressed sharply in suits, some paired with bow ties while others just wore braces. It gave her an odd chill when she thought about how many lives these men had taken; just how many deaths this room alone was accountable for. 

Once she reached the main hall, she let out a small gasp.  Large, circular tables covered in a white cloth filled the room. The centrepieces were tall five armed candelabra which rested on slates of wood, bottles of champagne stood chilled underneath waiting to be consumed. At the end of the hall, were two grand staircases, both snaking up to meet the small balcony that rested in the middle, looking over the entire hall. Y/N had been in some fancy places in her time, with all the high end clients she’d dealt with but this…this was something else. She didn’t know what she was expecting really but she knew that this wasn’t it. 

As they weaved through the sea of people, she felt Dean’s hand slide from the small of her back to the edge of her hip, his fingertips pressing into her skin slightly in a domineering manner. Looking around she noticed an array of eyes staring their way, groups of people whispering amongst themselves as they passed. It was in that moment, through the sea of people that she thought she had seen the bodyguard to The Master but her eyes quickly lost sight of him, her blood running cold. Why would he be here? She kept a small smile on her lips, playing her part as best she could as she turned to look at Dean whose jaw was ticking. He was pissed, that much she was sure of and he had every reason to be. Someone in this very room could be responsible for killing his parents; people in this room have done him and the Winchester family wrong.

Sam was the first to reach their table, the same table they had every year which was close to the grand staircase, in perfect view of the balcony that looked over the room. Y/N noticed how they were the first ones to the table, glasses unused and champagne bottles still chilled and corked. Dean pulled out the chair in front of him, resting his hands on the back as he motioned for her to sit down. With a polite smile, she did so before she tucked herself closer into the table. Dean’s hands gently came down to rest upon her shoulders, bending forward slightly so his warm breath tickled her ear as he spoke. 

“Going to get us some drinks, sweetheart,” he told her, his lips ghosting the skin behind her ear, “pick your poison.” He planted a soft kiss just below her ear as he waited for her response. Her mind was foggy as she tried her hardest to not concentrate on the feeling Dean was giving her, squeezing her thighs together tightly as his stubble grazed the nape of her neck. 

“There’s drinks on the table,” she said softly, her manicured hand gesturing gently to the unopened bottles in front of her. Dean just chuckled deeply, the rough noise vibrating through her skin. 

“With you looking like this, Y/N, I’m definitely going to need a stronger drink than that,” he husked quietly so only she could hear. 

“In that case, a martini would be lovely, thank you,” she breathed, biting down on the corner of her lip as she leaned to expose her neck ever so slightly to his advances. She felt how he smiled into her skin, his lips applying a little more pressure before he begrudgingly pulled away. With a nod to his little brother, he and Sam made their way over to the bar. 

At first she was shocked to see that he’d left her alone with no-one to watch her but that thought quickly passed when she remembered the freedom he’d given her without realising. This was her taste of a real life with no anchors; no ball and chain and she was starting to wonder how she was going to give it up. However, like a blast of cold air, reality hit her. This wasn’t a choice for her. Like it or not, she was going to have to give this life up in exchange for another one, one that had been fabricated by another client which she knew she wouldn’t enjoy. Letting a small, sad sigh pass her lips, she noted the 5 other free seats and wondered what time the rest of the Winchester family would arrive, eager to be surrounded by familiar faces. She wanted to get her plan underway, help show everyone at this Gala that they were wrong to not be working or be allies with the Winchesters. 

Before she could let her mind roam free anymore, a strong hand came to grip on her shoulder, fingers digging into her skin a little more fiercely than what Dean had done before. It made her dip her shoulder, struggling to free herself from his grasp before she turned in her seat. She was just about to tell Dean how he was hurting her when her blood ran cold. The eyes that she was staring up into were not the warm, emerald eyes of Dean Winchester. They were the cold, unforgiving eyes of The Master’s right hand man, Duke. Her stomach churned as he came to lower himself to her eye level, her gut instinct telling her to run but his grip on her was the reminder that she couldn’t go anywhere. 

“What are you doing here?!” he growled, his eyes boring into Y/N’s as he stared her down. She frowned slightly, confused as to why he would ask her that question.

“I-I’m working, what else would I be doing?” she answered, bewildered, her body tensing under his touch. Duke just curled his lip, shaking his head from side to side.

“You shouldn’t be here, you should be in Canada with Mr Orwig,” he snapped, his hand leaving her shoulder to the top of her arm as he prepared to move her.  

“Who?” she all but squealed, his fingers digging into her skin as she flinched, Y/N’s small hand holding onto his wrist as she tried to ease some of the pressure. “I’m sorry but Mr Winchester is who I am meant to be with. Take it up with Balthazar, he’s the one that introduced us,” she explained frantically, keeping her voice low and her answer vague as to not arise any more suspicion from onlookers. Duke was jeopardizing her job but her mind was doing overtime, Duke kept a separate log book of each girls location. It’s how he kept tabs on them to prevent runners so why didn’t he know this?

“Don’t play dumb with me, whore, you can save your smart ass answers for The Master,” he spat as he pulled on her arm, forcefully pulling her up from her chair into a standing position. Y/N couldn’t help but stumble on her heels, causing a few guests to turn and look in her direction. 

“T-the Master? He’s h-here?” she stuttered, her eyes wide and her skin cold as her stomach churned. She felt the bile rise to the bottom of her throat, threatening to surface as she thought about him seeing her dressed up like this. Duke just scoffed, looking her up and down with disgust in his features. 

“Don’t be so stup-” 

“-is everything ok here?” The deep rumble of Dean’s voice wrapped around her like a safety net, she let out a small sigh of relief when she glanced behind her to see his green eyes staring down her aggressor. She felt Duke release his vice on her, his body stiffening slightly when Dean took another step forward, snaking his arm around your back to your hip to pull you close. 

“Yes. Fine. Dean, this is an associate of mine. Works very close with the owner of the business.” She gestured towards Duke as she still kept her answers vague, she was very aware of her surroundings. “And as you can see, Duke, this is Dean. The man I was telling you about,” she introduced, swallowing hard as she watched Duke eye the man for longer than was necessary. Dean broke the tension by holding out his left hand for Duke to shake, a small smile on his lips as he waited. Duke returned the gesture, his gaze falling back onto Y/N as he did so. Dean released his hold on Y/N, his grip tightening on Duke as he pulled him closer, his shoulder pushing against his foe. It was a quick move, one that took Y/N by surprise. He bowed his head to Duke’s ear, his lips curled into a snarl.

“Don’t you ever fuckin’ lay your hands on my girl again, you hear me? You do, I’ll make sure that your licking the gates of hell before you can even blink. Am I clear?” Dean threatened, his words full of venom as his knuckles turned white from gripping Duke tightly.

“Crystal,” Duke replied, his eyes widened slightly from Dean’s threat. Happy with his answer, Dean pulled back and released the man’s hand, straightening his own suit before sliding his hand back around Y/N’s waist.

“Good, now excuse us, would you?” Dean all but shooed Duke off, turning his back to him as his focus became solely on Y/N. But her focus was on the Master’s right hand man as he stormed off into the distance, his phone to his ear. Her stomach churned as the colour drained from her face; he was calling the Master. She couldn’t help but wonder if she’d been in Dean’s company without the Master knowing. If that was true, he’d think she was trying to flee again; her life wouldn’t be worth living. 

“You ok, sweetheart?” Dean’s soft voice cut through her thoughts. Y/N blinked a couple of times, smiling slightly as she took in the concern that was etched in his features. 

“I’m fine, honestly,” she lied. She was shaken to the core but she knew she had to focus, she had a job to do. If she failed here, with her client, it’d only make matters much worse back at The Hemlock. 

“What did he want?” he asked her concerned, his warm palms rubbing gently at her arms to comfort her slightly. 

“He wanted to know why I was here and not in Canada, because apparently that’s where I’m meant to be,” she explained as she frowned. Her Y/E/C eyes looked up into Dean’s, silently asking him for an answer to this whole mess. His face softened at the look she was giving him, causing him to pull her into his chest, his arms wrapping around her frame as he did so.

“He got it wrong, Y/N. You’re where you should be, you have a contract that states that,” he whispered into her ear before his lips gently kissed the side of her head, as Y/N wrapped her arms around Dean’s middle. She allowed her body and mind to relax in his hold. She’d completely forgotten about the contract. The contract that the Master, Balthazar and Dean all have a copy of. The contract that states where she is, who she’s with and exactly how long she’s going to be there for. Just knowing she had that little bit of security made her feel a little bit more at ease with it all but it still didn’t shake the dread that was lying in the pit of her stomach. 

The sound of laughter and chatting brought her out of Dean’s hold, her head glancing just behind her to see the rest of the Winchester family making their way to the table. Benny, Cas, Charlie, Kevin and a man she thought she recognised. He came over to her, adorning a smug smile as he ran his hands over his slicked back hair. She pulled away from Dean’s chest, her hand instinctively going for his as the man approached her. Before he could even open his mouth, Dean held up his free hand in front of him, stopping the man from coming any closer to Y/N.

“Gabe. Just…don’t even start,” Dean sighed as he looked down at his date, “he’s my cousin,” he continued exasperated as Y/N bit back a grin, amused at the annoyance Gabriel was already causing Dean. 

“Enchante.” Gabriel bowed slightly, reaching forward for Y/N’s hand before kissing it gently.

“For the love of…” Dean muttered under his breath causing her to chuckle slightly.  

“Nice to meet you, Gabriel,” she replied politely. It was only when Gabriel sent her a wink did his face click in her mind. She’d seen him before, a few times if she was going to be precise. “Wait…I’ve seen you at The Hemlock,” she announced pointing at him as Gabriel’s eyes grew wide; his cheeks glowing red. 

“Yeah…Gabe here likes to spend most of his free time grunting between a woman’s legs,” Dean remarked, a small smirk on his lips as Gabriel feigned hurt. 

“Don’t be so crass, Cousin,” Gabe scolded, winking at Y/N to which Dean rolled his eyes. 

“Gabe, sit down and shut up,” Dean instructed to which his cousin followed. In that moment, Sam returned with the drinks, placing Y/N’s martini in front of her on the table before handing Dean his whiskey. Once again, Dean held out her chair as she tucked herself back in her seat. He ensured she was comfy before taking a seat next to her, sliding his arm around the back of her chair as he waited for his family to settle. Y/N automatically leaned a little more into his open body, her eyes raking over his features that the warm light of the room highlighted. The slight stubble on his cheeks, the few freckles that littered his skin; the small crinkles by his eyes; She enjoyed how the candlelight reflected in his green orbs, the small sparkle it gave them as he laughed along with his family. She watched how he’d wet his bottom lip every now and again after talking, her imagination going wild at what else he could be using that tongue for. 

The music dimming and the sound of silverware tapping on glass brought her attention to the balcony in the middle of the grand staircase. Chatter had eventually quietened down to a few hushed whispers as everyone looked up at the man standing there, his arms out wide as he announced his presence. Y/N recognised the man that was standing there. His name was Nick and he was the Don of the most powerful mob in this room. Some referred to him as the devil himself, earning him the nickname Lucifer thanks to some of the vile and violent acts he had under his belt. 

“Good Evening, ladies and gentlemen,” Nick bellowed across the hall, one hand on his chest whilst the other grasped at a glass of champagne. “First of all, I’d just like to say how amazing it feels to be standing up here, I’ve waited years for this moment and after poor John Winchester’s untimely demise,” he drawled, a smirk pulling at his lips as he looked down at the Winchester table, “God rest his soul,” he sarcastically consoled, “this role has now befallen on to me-” 

“-fucking asshole,” Dean spat, visually tensing next to Y/N as Nick continued his speech. Dean’s hand gripped harder at the back of her chair as he nursed the glass of whiskey that was in front of him. Y/N placed her hand on Dean’s thigh, gently squeezing to encourage him to look at her.

“Dean-”

“-our Dad used to stand there every year, in that exact spot and talk about greatness. Only the most powerful Don gets to introduce the Gala and it’s been my dad for the past six years. He’d commend the ones that had earned it, share stories about his past year and encourage everyone to get to know everyone. You wouldn’t think the room was full of murderers, drug traffickers and the rest. But this guy?” he spat, gesturing towards Nick before placing his now empty glass back on the table, his fingers tracing the edge. Y/N angled her body to face him, bringing her soft palm up to caress his cheek, encouraging him to look at her. 

“Dean, take this as a lesson instead of allowing it to anger you. Nick is gloating, flaunting his power over everyone else in the room. He’ll lead by using fear whereas your dad led by using the respect given to him. It’s how he stayed so powerful, he was respected as well as feared,” she explained, her words soft but clear. “The Winchesters will get that spot back, I promise you.” With that, she placed a soft kiss to his stubbled cheek causing her lips to tingle as the smell of his cologne engulfed her. 

Dean didn’t reply, instead he just closed his eyes and relished in the feeling of her lips upon his skin. When she parted from him, he felt himself missing her touch; missing the warmth she provided. So, he pulled her closer, allowing her to lean into him as his arm left the back of her chair to rest over her shoulders, his lips choosing to leave a soft, lingering kiss on her temple as his fingers ghosted across her skin. She briefly closed her eyes and allowed herself to embrace this feeling for a moment, the closeness, the intimacy. She allowed herself to think that this was real but as she slowly opened her eyes, they fell on Duke who was sitting a few tables over, an evil smile resting on his features as he watched her. She broke his gaze, trying to act unaffected by his stare as she tucked herself into Dean’s shoulder, trying to take comfort in his closeness. She had to play tonight just right and knowing that the Master now had eyes on her, the pressure was on.


	17. Chapter Fifteen

**Notes for the Chapter:**

> This is a bit of a longer one - but i hope you enjoy! We're at the halfway point ;) 
> 
> If you like it, let me know your favourite part, your theories and thoughts! I love to hear them. 
> 
> Love you all 
> 
> -Winchest09

The Gala had been underway for around two hours, dinner had been served and consumed and now the attendees were happily talking between themselves. Duke had disappeared into the crowd pretty quickly once Nick had finished his speech; something that didn’t sit well with Dean. Due to this, he had given Sam, Benny and Cas the heads up and they gave their word that they would keep a lookout for him, knowing to keep Duke as far away from Y/N as possible. 

Glancing to his side, he watched how Y/N giggled at a story that Gabriel was telling. Her petite manicured hand curling around the stem of her martini glass as she listened intently to what his cousin had to say. The longer he stared, the more his brain filled with thoughts and ideas of what her life must be like. He was worried, her behavior after Duke had changed somewhat and she’d become almost fearful. The way she huddled into his side as if she was yearning for his protection. His gut was telling him to tread carefully, so that was what he was going to do. 

Breaking his concentration from Y/N and Gabriel, Dean took a long sip of his whiskey. Savouring the flavour before allowing the amber liquid to delightfully burn the back of his throat as he glanced around the room. He was analysing everything and everyone, who spoke to who and what mobs stood together. He needed to piece together a plan to gain more business; he knew Y/N already had one but Dean loved a back up. Peering through through the crowd, one hand on the white tablecloth with the other firmly wrapped around his glass, he spotted a very familiar pair of brown eyes staring back at him. It made his jaw tick, stomach churn and grip on his glass tighten. 

Cassie Robinson.

Her dark hair curled just past her shoulders, her lips painted red as she leant forward on her table giving Dean the perfect view of her breasts. She wore a tight fitted champagne gown, squared off across her chest to show off her assets but Dean wasn’t interested. The feeling of her betrayal still at the very forefront of his mind. He’d loved her, he’d looked after her, he had given her everything she could possibly want only to have her stab him in the back. She ran from his home, an array of plans and documents hidden away in her handbag as she hurried back to her Don, the one calling the shots and pulling the strings all along. Zachariah. 

He didn’t know how long he’d been staring at her for nor how long he’d held her gaze but the feeling of a warm hand on his made him look away. Looking down, Y/N’s fingers curled around his, encouraging him to look at her as she gave him a warm smile. He couldn’t help but notice the warmth that encased him with her touch; how she only had to look at him with those sparkling Y/E/C eyes for him to be calm.

“You alright, sweetheart?” he asked, his voice low as he turned his body to face her, his thumb running over her fingers in his grasp. 

“I think it’s time we go and mingle,” she suggested, a slight smile on her lips as she raised her eyebrows once, letting Dean know that it was time to work. 

“You’re right,” he agreed, bringing her hand up to his lips to give her an appreciative kiss before he stood from his seat. “Come on, I know just where to start,” he offered, helping Y/N stand before he pulled her close to his side. 

She wrapped her arm around his middle and he allowed a smile to pull at the corner of his lips, her intoxicating perfume washing over him. He watched how she gracefully walked beside him with her head held high, how she took in everything that was happening around her. She fit so naturally with him, almost like she was made for his world; made for him. He shook his head slightly at the thought, his mind telling him that she was just ridiculously good at her job. It was her profession to blend in wherever she went but he couldn’t help but think what if? What if she could stay by his side, she’d already helped so much with his business and as he guided her around the room, he was astonished to see just how many people fell under her charm. 

He’d introduced her to Abaddon who became entranced by Y/N almost immediately, appreciating the tenacity and knowledge that she had. Next on his list was Ketch, British by roots but had settled into American life fairly quickly. Dean was keen to have Ketch on side, knowing that his connections to the United Kingdom could prove fruitful in the future so as he watched Y/N work, he became hopeful that it could soon become a reality. With every passing minute, she impressed him more and more, his hold on her tightening, never wanting to let her go. 

Ketch politely said his goodbyes, handing Y/N his business card telling her to call him to arrange a meeting. With a beaming smile, she turned to Dean and looked up at him from under her long sooted lashes, casually handing over the card to him for safekeeping. She gave him a look that made him catch his breath, his heart pounding against his chest as he lost himself in her eyes. She gave him a look that silently asked him if she was doing ok but his voice got caught in his throat so he allowed his actions to answer. He brought up his hand from her waist, his fingers ghosting over the edge of her jaw before he brushed his thumb affectionately over her cheek. Her hand came to wrap around his wrist, leaning into his touch which made his heart swell. 

“Dean Winchester, long time no see, baby.” The sound of her voice made Dean’s skin crawl. He quickly pulled his hand away from Y/N’s face before sliding it back around her waist, pulling her close to his side. His eyes darkened as he glanced up at the sleek figure that stood in front of them, a smug smile on her lips as she sauntered closer to him. Her long fingers coming to play with his tie as she turned to face Y/N. “I’m Cassie, I’m sure Dean’s told you  _all_ about me,” she taunted, patting Dean’s tie back down on his chest before grinning mischievously. 

“Not that I can recall to be honest,” Y/N casually replied with a shrug of her shoulders, causing Dean to hold back a smirk when he saw how Cassie’s face dropped, her lips curling slightly in disgust as she frowned. 

“Who are you?” Cassie grunted, looking Y/N up and down judgmentally, causing Dean’s grip to tighten on her. 

“Y/N,” she introduced, angling her body so she was snuggling closer into Dean. Her hand now coming to rest on his chest the same way Cassie was doing just a moment ago. He could only hope that she wouldn’t be able to feel the way his heart was beating wildly. 

“Ah, I’ve heard of you. It seems that you’ve got our Dean here wrapped around your finger. Oh, and Crowley for that matter,” she scoffed, her finger coming to play with a curl in her hair as she looked Y/N up and down. Out of his peripheral, he noticed a familiar figure come into view.

“Cassie,” the elder voice scolded, his hands coming to rest on the tops of her arms, “that’s no way to introduce yourself to Dean’s new  _friend,_ ” he drawled, a sly smirk resting on his lips as he stared down Dean. 

“Y/N, this is Zachariah,” Dean introduced, gritting his teeth as he clenched his jaw. If anyone got under his skin, it was him. He watched how Zachariah’s eyes roamed over Y/N’s figure causing him to press a soft kiss to her temple. It was a power play, one that told the older Don that she was off limits and exactly who she belonged to. The move didn’t go unnoticed by Cassie who pulled herself away from Zachairah, an irritated growl leaving her lips. 

“So, come on, let me in on your secret. How do you do it?” she pried, walking closer to Y/N who was just looking back at her, a little perplexed. Cassie just shook her head, looking her up and down. “Let me guess, your knees are a little bruised and your legs ache from being open all day, huh?” she taunted, a little laugh passing her lips. Dean felt the anger surge within him, his pent up hate for the woman in front of him threatening to be unleashed.

“Cassie,” he warns, a low growling tone to his voice. However Cassie paid it no mind, ignoring the green eyed Winchester to carry on picking at Y/N. 

“No, come on, I want to know what’s so captivating about you. You can’t seriously tell me you got where you are without putting out a little. Please, share it with the class,” she laughs half heartedly as she turns around to gesture to the rest of the room. A few of the closer guests were now watching this sudden confrontation, intrigued as to where this commotion had come from. Dean just huffed as he squared his shoulders, looking down at the woman that once shared his bed.

“Why? You feel threatened?” he asks, his words lined with venom. Cassie just laughed, her hand coming to her chest as she pointed at Y/N.

“By this? Please.” She shook her head, an amused grin on her lips as she looked between them both. She began to saunter over to the eldest Winchester, her hands now resting on her hips over her champagne dress. “Besides, Dean, I think you’re forgetting who brought you to your knees the first time round.”

“And I think you’re forgetting the error you made with your  _magnificent_  plan.” The sudden sound of Y/N’s voice made Dean’s heart jump, glancing down to the woman on his arm, her face hardened as she stared down Cassie. He bit the inside of his cheek, if he knew Y/N at all from the time they’d spent together then he knew that she was about to unleash some  _well researched_  home truths.  

“Excuse me?” Cassie scoffed, turning her attention back to the Y/N, who was slipping her arm from Dean’s back so she could use her hands to emphasise the point she was about to make. 

“Sure, you stole some plans from Dean and may have had him fooled for a moment, but I doubt that you’ve realised that you’ve royally screwed yourself over,” Y/N explained, her voice just loud enough so the onlookers would hear. “Everyone knows about your dirty little trick so ergo, no-one in this room will ever want to trust you again. Everyone will be dubious of any alliances that you and Zach here want to make. You played your only card, Cassie, and you played it foolishly. You won’t be able to get close to  _anyone_  ever again because everyone in this room knows what a devious little bitch you are.” Y/N stared Cassie down and Dean had never been more attracted to her. The way she handled the situation, how she portrayed herself as she retaliated to Cassie’s taunts; she was perfect. 

“I…well…” Cassie stuttered, words unable to leave her mouth as she looked around at all the eyes that were watching her in the room.

“Come, Cassie, we have other business to attend to,” Zachariah muttered, quickly placing his hands her shoulders before pulling her away from the crowd. Dean couldn’t help the wide spread grin that crept onto his face as he watched them walk away, nothing but pride filling his chest as he looked down at the woman he was slowly, yet unknowingly, losing himself to. 

“Damn, Y/N.” He couldn’t help how gruff his voice sounded, going to clear his throat when he looked down to see her wide eyes; almost as if she was panicking that she’d stepped out of line.  

“Sorry if i-”

“-don’t you dare apologise, that was…” He didn’t have a word for it. He was impressed, he was blown away; hell he was even turned on. He saw a spark in her that made him yearn for more. He quickly turned her in his arms, both of his large hands coming up to cup her face as he smiled down gently at her. He gently pushed her hair out of her eyes, his thumb coming around to pad softly at her bottom lip.  _Goddamn_  how he needed her; how he wanted her. 

For the first time in a week, he brought his lips to hers. He breathed her in, trying to remember everything he could about that moment. How soft her lips felt, the way she was gripping onto his shirt; the way she tasted. She hummed against his lips, a soft moan sounding from her as he traced her bottom lip with his tongue. He was doing everything he could to restrain himself, to hold back from finding a private room and having her there and then. 

Resting his forehead against hers, he tried to steady his breathing, watching how Y/N was doing the same. She smiled widely, her cheeks glowing slightly as she focused on straightening his tie. In that moment, the rest of the room was forgotten. All Dean could focus on was her. But, like a bucket of cold water, somebody clearing their throat caused Dean to straighten up. 

“Well, Y/N putting Cassie in her place was certainly entertaining,” a British voice commented, causing Dean to look to his right. “I think we all know not to trust Cassie and her group of dogs.”

“Good Evening, Fergus,” Y/N greeted, smiling widely as she turned to Crowley, her hand coming out to meet his.

“Lovely to see you again, my dear. You look radiant,” he complimented, kissing the back of her hand, “Dean,” he greeted, raising his glass of scotch in acknowledgement.

“Crowley.” Dean nodded, ensuring to slide his hand back around Y/N’s body slowly, his fingers softly circling on her hip. 

“Still happy with the shipments?” Y/N asked, eager to ensure that business between them was still good, her own fingers coming to rest on Dean’s as she smiled sweetly. There was a delayed pause as Crowley slowly sipped on his drink, his eyes wandering over to Dean before they landed back onto hers. 

“Indeed,” he agreed with a smile, shuffling closer to Y/N. “It appears you were right my dear; there is a lot of money to be made in genocide.” He winked at her, a smug smile tugging at his lips as his hand into his dark suit. 

“I’d hate to say I told you so…” Y/N almost sang, jesting with Crowley. The British man just nodded in agreement, not wanting to admit aloud that Dean’s deliveries had been very beneficial indeed. Crowley finished his scotch, holding the empty glass in his hand as he pointed towards Dean. 

“We must meet again soon; have dinner. I have a few more propositions for you both that I’ll think you’d quite like,” he suggested, earning a nod from Y/N as she curled herself into Dean’s body. 

“Sure, we’ll check appointments and give you a call.” Dean nodded, flashing Crowley a small smile as he tried his hardest to not focus on the warmth that was emitting from Y/N’s body. Crowley nodded curtly, flashing Y/N a smile before he headed towards the bar. Dean couldn’t help but feel elated at how well Y/N was working at this Gala; at how she was winning over contacts and potential allies with her knowledge and charm. 

As his mind wandered, Y/N turned in Dean’s grasp. Her hands slowly sliding up his chest and she hummed her appreciation of the muscles tensing under her touch. Her fingers rested on the nape of his neck, playing with the small strands of his hair as she looked up at him, gently pressing her body against his. Dean couldn’t resist her; she was hypnotising. He bowed his head slightly as he searched once again for her lips, capturing them with a kiss. His hands tightened his hold on her hips, pulling her as tight to his body as possible. The way she kissed him, the way her nails gently scratched against his neck, the way her body melted into his; it was sending him crazy. He didn’t want to stop, her lips were soft and she tasted sweet. The noises she was making, the way her breasts were pressed tightly against his chest; Dean was beginning to lose himself in his head. Imagining how her soft skin would feel under his rough fingertips, how her naked form would feel weighted on top of his; he needed to calm down. Therefore, he reluctantly pulled his lips from hers.   

“We should,” he husked as he rested his forehead on hers, “we should probably continue with the plan,” he finished, letting his tongue trace along the bottom of his lip. His pine green orbs kept flicking down to her now swollen lips and he couldn’t help but smile when he noticed how her lipstick had smeared slightly. His reaction made Y/N let out a little laugh, bring her fingers to her lips as she knew exactly what he was smiling at.

“I think I’ll need to freshen up before we carry on,” she giggled, her cheeks tinted a shade of pink, “won’t be too long." 

"Sure,” Dean agreed, reluctant to let her go. He watched her carefully as she gracefully filtered through the crowd towards the bathroom, his eyes never leaving her form. With Duke around, he needed to ensure she was safe but at the same time, he didn’t want to be chaperoning her wherever she wanted to go, especially not to the bathroom. A lady deserved her privacy. 

Whilst his eyes were trained on Y/N’s figure, Dean was unaware of the commotion that was erupting just behind him. A waiter had stumbled, causing him to fall onto another guest at the party; thus causing a domino effect. Dean didn’t see it coming when a heavy force knocked into his back causing him to stagger, the shock of the blow causing him to lose sight of Y/N. Instead, his focus was on the young man that was looking up at him from the floor, cowering. Dean just rolled his eyes and offered him his hand to help him up. When the young man was fully stood, Dean’s eyes immediately went back to the last place he saw Y/N, his eyes scanning the crowd frantically as he tried to find her. 

-

Y/N looked at herself in the mirror of the bathroom, the stalls quiet as she appeared to be the only one in there. She couldn’t help but smile at her reflection, the way her red lipstick had smudged across her lips was a reminder of the way Dean’s lips felt against hers. She was on cloud nine. She didn’t want to correct the smears, she didn’t want to wipe away the evidence of his kisses but she knew she had to look presentable. With that in mind, she grabbed a few tissues from the box that was on display on the countertops before she began to carefully rub away the red stains from around her lips. Once she was cleaned up, she proceeded to reapply her red lipstick to her still swollen lips before she took one last look at herself in the mirror. The night was going well, she was winning meetings for Dean, she was strengthening bonds with other mobs, she was doing her job well. With a deep breath, she ran her hand through her hair and told herself:  _You’ve got this._

Y/N pulled open the heavy bathroom door, eager to get back to Dean as soon as possible. She frowned slightly when she wasn’t greeted with a busy hall like the one she came through originally, it was quiet and it made her feel a little uneasy. She began to quicken her steps, knowing she’d be safe in Dean’s arms once she got there. She wasn’t expecting to feel two strong hands grab ahold of her arms, pulling her into an adjacent room before she even had time to let out a squeal. She heard the door slam shut before she was spun and slammed up against the cold wall. She winced, pain shooting down her spine causing her eyes to shut momentarily. When they opened, her captor was staring her down, his eyes dark as a malicious smirk grew on his lips.  _Duke._

“I’ve been informed to teach you a lesson, whore,” he spat as he moved his arm to push against her chest to keep her in place; pinned against the cold concrete. The moment The Master’s name spilled from his lips, Y/N felt the blood in her veins run cold. 

“W-what?” she stammered, trying her hardest not to panic, her hands coming to grab at Duke’s bicep to try and relieve some of the pressure he was putting on her chest.

“The Master is not pleased with you, Y/N,” he growled, his face coming close to hers, his nose rubbing against her neck as he breathed her in. “Told me to remind you who you belong to,” he murmured against her skin, a low groan passing his lips. “I’ve always wanted to know how it would feel to have my cock in your mouth.”

That final sentence made her stomach churn with fear and her eyes widened with panic. No, not here, _not this._ She’d done everything that she’d been asked to do, where had she gone wrong? Her thoughts were interrupted when she heard Duke’s fly open, he was using his free hand to pull out his already erect cock. Y/N shook her head violently, her state of panic increasing. She had to scream, she had to cry for help. She knew it would get her in more trouble once she got back to The Hemlock but she had to do  _something._ She took a deep breath, readying her lungs for her inevitable cry when Duke’s large hand came to wrap around her throat, squeezing tightly at her windpipe. Her hands immediately went to claw at his on her neck, desperately trying to pull him off of her, nothing but tiny gasps and squeaks passing her lips. She could only watch on as he forced his body weight on her, his lips gracing over her neck as he grunted. He pulled back, rippling his fingers over her neck to reaffirm his grip with an evil grin. She felt how her strength was beginning to fade, darkness clouding her vision as she tried hopelessly to stay conscious. So when a darkened blur came rushing into her tiny field of view, she didn’t know if it was her imagination hoping someone was saving her. It was only when she was able to heave a deep breath did she realise that it was in fact, a reality. 

She tried desperately to focus on what was happening around her, gasping for breath when she felt another pair of hands on her. Frantic, she turned around to lash out but when she was met with a pair of blue eyes, she calmed. Benny. He quickly gave her a once over before moving her towards the door where Cas was standing watch. That was when it clicked with her -  _Dean._ She spun on her spot, holding Benny for balance as she looked to where Duke was. Sure enough, Dean was beating the shit of him. Before Y/N could blink, Dean had spun Duke and pressed him face first against the concrete wall she was pinned on moments ago, Duke’s arm twisted around his back. Dean had his fist gripped in Duke’s hair, his expression deadly as he pulled Duke’s head back and slammed it against the wall.

“It appears that my earlier warning wasn’t as fucking crystal clear as I thought,” Dean snarled, venom spitting from his lips as he pressed Duke’s face harder into the concrete. Y/N began to panic once more, she didn’t want this to go back to The Hemlock, she didn’t want her already earned punishment to get even worse but most importantly, she didn’t want Dean to get hurt.  

“Dean, don’t!” she pleads but it fell on deaf ears. Dean paid her no mind, his sights were set on Duke. He was like a bull with a red flag and he wasn’t letting up. 

“So let me say it in a language that you’ll understand,” he spat as he once again pulled Duke’s head back before slamming it as hard as he could against the wall. “Don’t you ever-”  _slam,_  “fuckin’ touch-”  _slam,_  “my girl again.”  _Slam._   “I don’t give a shit if she works for you. I don’t fucking care about your hold over her. She’s  _mine,”_ Dean growled as he forcefully pushed harder on Duke’s head, blood and bits of his skin covering the concrete where Dean had continually smashed the assailant’s head. Y/N watched with wide eyes, her mouth slightly agape as her hand tried to massage the sore spot on her throat. It was only when Duke started to laugh, did she feel the bile rise from her stomach.

“Just until your contract runs out. Then, she’s  _mine,”_ Duke taunted through gasps of breath as he smiled, revealing his blood covered teeth. Y/N saw how Dean curled his nose and clenched his jaw, the anger evident in his features. 

“We’ll see about that,” Dean snapped before ramming Duke’s head as hard as he could back into the wall, knocking him unconscious. His body fell to the floor in a slump as Dean immediately made his way over to Y/N. He softly brought his hands to her face, silently checking if she was ok. He frowned slightly when he noticed the angry red marks that were littered over her skin.  However, before he had the chance to speak to her, a commotion was heard outside of the room. With a thud, the door swung open with a number of security that hastily entered, their eyes landing on the bloody slump against the wall before moving over to Dean. No questions had to be asked, they could see clearly what had happened and swooped in to grab a hold of Dean and YN to escort them off of the premises. Before they could even come into contact with them however, Dean squared his shoulders and moved Y/N so she was standing behind him.

“Don’t you dare lay your hands on me or her! We’re going,” he shouted, anger pumping through his veins as he turned on his heel to walk out. He softly placed his hand on Y/N’s wrist before he began to pull her along with him, Cas and Benny not far behind him. As he exited the room and made his way to the foyer, he noticed his brother rushing towards him, confusion written on his face.

“Dean?” Sam asked, frantically looking between him and Y/N as he came to a stop by their side. Dean just sent his little brother a look, a long silent pause between them as they silently communicated the severity of the situation. The sound of a deep groan caused Sam to look over Dean’s shoulder, his eyes falling on the two members of security who were carrying Duke from the room, his face bloody, swollen and beaten. Sam swallowed hard before looking back at his brother who gave him a knowing look. 

“You guys stay. Sam, do some damage control and keep an eye on that dick,” he grumbled as Sam nodded. Dean started to descend the stairs, gently pulling Y/N along with him before he stopped, turning back to face Benny and Cas. “Oh, and you two,” he all but shouted, pointing between them both,“when I tell you to do something…fucking do it,” he fumed.

“Yes, Boss,” Benny muttered, nodding his head towards Dean. With that, the eldest Winchester descended the rest of the stairs, thankful that Garth was already waiting in the courtyard with the Range Rover. He told Garth to start the engine before opening the back door for Y/N to get in. 

She did as she was told, her one hand coming back up to rub at her throat as Dean slammed the vehicles door behind her. She winced at the force he used to close the door, a sense of shame washing over her causing her to look down at her dress, picking at the material. Dean entered the other side, shutting his door forcefully before he barked at Garth to drive home. 

The ride was awkward. Silent. Nothing but the sound of them breathing filled the air around them. Y/N couldn’t look at Dean but she noticed out of her peripheral vision that he was staring out of the window. His body was rigid, one hand resting on his leg whilst the other was leaning against the door, supporting his head. Y/N couldn’t speak, each word she tried to form in her mouth failed to pass her lips. She was embarrassed that all of this happened because of her. Because she had gone wrong somewhere, because The Master was upset with her; she’d ruined Dean’s evening and the plan they had. She’d ruined her chances with Dean. 

As Garth pulled up in front of the Winchester Manor, Dean didn’t waste a minute as he jumped from his seat and got out of the vehicle. Y/N’s head shot up at the sudden movement and she watched him storm around the back of the Range Rover and up towards the front door. He hadn’t stopped to help her get out, he hadn’t stopped to ask her if she was ok and by the way his shoulders were tensed, she knew she was in trouble. 

She hurriedly gathered her dress and climbed out onto the gravelled front yard, Garth trying his best to assist her. Knowing she’d reach Dean faster without her heels, she hurriedly pulled them off her feet before she rushed to catch up with him, not caring that the gravel was digging into her skin. She moved as fast as the dress would allow, pushing open the front door just in time to see Dean disappear down the corridor that led to his office. 

“Dean, wait!” She called, panic in her voice as she hastened her movements once more but he didn’t stop, he carried on storming towards his office doors, anger evident in his form. She watched as he threw open his door, turned on the light and moved behind his desk. She heard him opening all his drawers, rushing to look through each one before slamming them shut when he didn’t find what he was looking for. When she made it to the open door, she threw her heels down onto the floor next to her, her heart beating wildly in her chest.

“Look I’m sorry, ok? I’m really sorry,” she pleads, fear creeping into her soul at the thought of him being this angry with her. Dean just shook his head as he lets a scoff leave his lips, continuing to search his desk.

“Sorry?” he questions, his brows knitting together in confusion before he shook his head, “I need to speak with your boss,” he continued, his voice a mumble as he moved some of the documents off the top of his desk. Y/N knew he was looking for her contract, the one that had The Master’s phone number on it in case of any complaints. 

“Dean, no, just leave it,” she panicked, rushing forward to stand on the opposite side of his desk.  “Please, I’ll do anything,” she pleads, her eyes glassy as she continued to stare at Dean. His jaw clenched and his hands became tightly fisted on top of his desk as he leant down on his knuckles.

“Leave it?!” he snarled, his gruff voice shooting through her as his now darkened eyes came to stare into her own. She felt herself retreat slightly, the sight in front of her was dangerous. “Y/N, he had you by the throat,” he spat, shaking his head as he wiped all of the stuff off the top of his desk in one, strong action. 

“I-it’s fine,” Y/N stammered, looking around at the mess Dean had just created, papers littering the floor. She was trying hard to wrap her head around everything that had happened in the space of an hour. 

“Fine!?” Dean snapped, scoffing in disbelief. “He was going to force you to suck his dick and you think that’s fine!?” The volume of his voice had risen causing Y/N to go wide eyed. 

“No, I-just,” she stumbled over her words as she tried her hardest to think of what to say to calm the situation down. She was failing. 

“Plus that dick ruined my evening, ruined  _our_ plan to get  _my_ business back on track, that’s what I hired you for so I think I’m allowed to say something,” Dean ranted, heading over to where the filing cabinet stood, hoping the contract would be in there. Y/N rushed forward, her hands coming to wrap around his arm as he pulled open the first drawer. 

“Dean, please, I’m begging you. It’s not worth your time. I know you’re angry with me but I’ll fix this,” she promised, pleading in anyway that she could. She knew that she was already in for an inevitable punishment anyway. When Duke shows up beaten and bruised, she knew she’d get the blame. If Dean rung up and complained, The Master would only come down in her like a ton of bricks. She didn’t want to think about how bad her punishment would be, she couldn’t let it happen. 

“Not worth my time? Angry with you?” Dean’s voice had softened and when Y/N looked up to meet his eyes, she noticed how his face had relaxed into a state of concern. “Sweetheart, Duke had you pinned up against a wall, his fingers were wrapped around your neck that tight you couldn’t breathe and you think I’m angry with you? That this is not worth my time?” he asked her softly, his voice gruff as he slowly shut the filing cabinet drawer. Y/N just shook her head, releasing her hold of Dean’s arm as she stood back. 

“Look at me Dean. I’m just an escort. People pay for their fill and move on.” She gestured to herself before bringing her hands up to her face to rub at her cheeks. She was doing her damndest not to cry as he gaze fell to the floor. 

“Just an escort?” Dean asked her, sadness evident in his voice. “Y/N, you’re so much more than  _just an escort._ ” He stepped forward, his feet coming into her view. Her eyes were glassy as she bit the corner of her lip. She felt Dean’s hand come up to cup the side of her face, his fingers edging under her chin to encourage her to look at him and not the floor. His eyes scanned her face, his expression softening when a stray tear fell down her cheek. “You have no idea of your own worth do you?” he whispered as he came to tuck some stray hair of hers behind her ear. 

Y/N didn’t know what to say. She was certain that she’d upset him, certain that she’d ruined everything but she was wrong. The way Dean was caressing her cheek with his thumb, the way he was looking at her told her everything she needed to know. He cared about her. He had saved her from Duke, twice. If only he could save her from this life. 

Determined to thank him, Y/N inched her face forward and pushed her lips against his. She kissed him with everything that she had, pressing her body hard against his as she slid her hands up his chest. Dean eagerly responded, his large hands coming down to grab at her hips to pull her closer to his groin. She moaned against him, allowing her tongue to trace his lip as she desperately wanted to deepen the kiss, something that Dean instantly allowed. 

She felt her arousal beginning to pool between her legs and the longing ache she had for him to be inside of her. She didn’t care about bets or contracts, in this moment all she cared about was Dean. She cared about how he was making her feel, how his stubble was slightly grazing her skin and how his kisses were making her lips swell. She cared about how his hands were squeezing at her hips, his fingers slowly indenting in her skin and the soft pleasurable noises he was making. She allowed her hands to slide back down his chest towards the edge of his waistband, her fingers tracing the materials edge which made his stomach twitch. An action that made her smile in his kisses. She lowered her hands even further, hearing how Dean’s breathing became ragged only for him to let out a low growl when she ran her palm over his erection. 

He wasted no time after that, his kisses became more desperate as he left her lips in search of her neck. Soft gasps left her lips as he nibbled and sucked at her pulse point, her hand still rubbing over his hard cock. He stripped himself of his suit jacket, his lips not once leaving her skin before he began to undo his tie. Y/N moved her hand to pull at his shirt, freeing it from where it had been tucked into his suit paints as Dean pulled his tie through his collar. She began to undo each button slowly, her hands shaking slightly from the excitement and adrenaline that was coursing through her veins. The feeling of his warm skin under her fingers causing her to have fresh waves of arousal. Dean moved around her, his hands coming to undo the back of her dress as his lips attacked the other side of her neck. All she could do was let her hands fall by her sides and concentrate on the feeling of Dean’s stubble burning against her shoulder. When she heard the sound of material ripping, she gasped, Dean clearly becoming impatient. In less than a minute, her dress was pooled at her feet leaving her standing there in nothing but her lacy, blue, underwear. She turned slowly to look at Dean, nerves slightly bubbling under the surface as he stood back. Her chest was heaving with each breath she took.

“God  _fucking_ damn, sweetheart,” Dean growled, palming himself as he took all of her in. He rushed towards her, his hands sliding around her sides and up her back as he kissed her once more. She’d never felt so wanted in her life. 

She placed her hands flat against his bare chest, his open shirt sliding down his arms slightly as she pushed him back towards his office chair. His thighs connected with the leather before he took his cue to sit down, his lips leaving hers. He swallowed hard, his stare never once leaving Y/N’s as she came to settled between his legs. Her fingers made light work of his paints, pulling the material down slightly to reveal his impressive length. She couldn’t hide her reaction, her eyebrows raised slightly, the corner of her lips turning upwards as she took him all in. 

“Like what you see, baby?” Dean teased, his hand coming to stroke his cock lazily as he looked down at her in want. 

“Oh, you bet I do.” She leant forward, using the tip of her tongue to trace the vein in his cock from the base to his tip causing Dean to let out a pleasurable hiss. He held himself at the base and watched how Y/N took him into her mouth, her red painted lips wrapped around him before he let go. He couldn’t help the low groan that left his lips as she worked him. The feeling of her warm, velvet tongue on his cock was enough to send him over the edge right then and there. Y/N moaned around him, loving the way he felt in her mouth, loving the way he tasted. She squeezed her thighs together desperate for friction. She’d never wanted anyone more. 

Dean threw his head back against his office chair, the luxury leather cool against his clammy skin as he took ragged breaths. Waves of euphoria washing over him as her mouth milked his hardened cock. He felt her fingers graze over the skin of his chest, her touch as soft as silk as she moved his crisp white shirt to expose his toned abdomen. Dean fisted her hair in one of his hands, encouraging her to work harder. His other hand gripped hard at the edge of the mahogany desk, knuckles turning white. He concentrated on the feeling, her hot tongue swirling around the head, the way the sound of her moans vibrated against his cock, the way she took  _all_ of him without a gag or a splutter; it took every ounce of control he had to not cum inside her pleasing mouth.

He bowed his head to look down at her. He watched how some saliva escaped from her pretty lips as she bobbed her head down his shaft. One of her delicate hands wrapped around his thick base, the other massaging his balls as she worked. He wasn’t going to cum like this and the tug on Y/N’s hair let her know that. With a reluctant pop, she released his cock from her mouth but not before using her tongue to slowly lap up the moisture she had left behind. Dean growled, his eyes catching hers as he watched her plump lips suck what cum he had just leaked from his tip.

Dean leant forward and grabbed Y/N by the tops of the arms, roughly pulling her up to adorn his lap. He wrapped her legs over him, his cock nudging at her cloth covered entrance as he attacked her lips with his own. Her hands clawed at his hair as he massaged her lips with his own, his hands making light work of the clasp of her bra. Pulling back from the kiss, he took a moment to drink Y/N in, slowly lowering each strap of her bra down her arms, releasing her breasts from their confines. With a smug grin, Dean threw the garment behind him, his tongue coming out to run along the bottom of his lip.

“Y/N,” he husked, taking her breasts into his hands and kneading them. “This is definitely one way to break your contract,” he continued, his lips grazing the nape of her neck, “and to think I almost didn’t hire you.”

“You almost didn’t hire me?” she asked shocked, pulling back from him slightly with a coy smile on her face. When she looked at Dean’s smug grin, she knew he was only joking. “You liar, you wanted me and you were determined to get me,” she gasped, feeling Dean’s fingers press slightly over her soaked panties, his thumb finding the edge and pulled them over to one side to reveal her pussy to him. He slid his fingers through her slick folds before slowly pushing them knuckle deep into her causing Y/N to gasp loudly and throw her head back at the feeling. 

“You’re right. Your talent, your skills, that mouth…” he groaned, the feeling of her warmth wrapped around his fingers was tantalizing, “of course I was determined to get you,” he finished before he started to pump his fingers in and out of her. His thumb nudged at her clit, causing her to jolt in his lap before he continued to rub slow circles as his fingers worked her. She could only moan, her hands gripping onto him tightly as she felt her coil in her stomach tightening. She bit the corner of her lip to stop her from screaming, an action that only made Dean work her harder causing her to inevitably let go around his fingers, her pussy pulsing around him as she moaned his name repeatedly. He quickly withdrew from her, placing his hands under her thighs to lift her onto his desk as he stood. His pants falling around his ankles as he spread her legs wide, her slick glistening in the light. 

He captured her lips in another searing kiss as his fingers left slight indents on her thighs. He slid his calloused hands up to meet the hem of her panties, his rough fingers wrapping around the material to pull them down her legs, dropping them to the floor. He admired her for one more moment, one hand coming to caress her face whilst the other wrapped around his cock, guiding it to her entrance. He entered her slowly and she gasped at the feeling, the burn she felt as she stretched to accommodate him. 

“You’re so fucking beautiful,” he complimented, his voice slightly breathless at the feeling of being buried to the hilt inside her, at finally being where he’d wanted to be. His hand slid from her face to her shoulder, pushing her backwards until she lay flat across his desk, his other hand coming to hook her leg over his shoulder as he started to thrust hard and fast into her. The way her breasts were bouncing with each thrust, the way she clenched around him; he couldn’t help the low growl that left his throat. “And you’re  _mine_.”


	18. Chapter Sixteen

**Notes for the Chapter:**

> Sorry it took so long guys - here his Chapter 16. I hope you enjoy it, we're on the edge of some interesting events!

The morning sunlight broke through the small gap in the thick cream curtains, casting a ray of warmth over Y/N’s face. With a few soft blinks, she woke up slowly, taking a moment to just appreciate the quiet that surrounded her. She pulled her cover closer to her body as she smiled, the burn between her thighs and the pleasant ache in her centre being a wonderful reminder of the sex she had with Dean. It was everything she thought it would be and more, he’d made her orgasm in a way that no other man had ever achieved. Her toes curled, her screams were silent and she was pretty sure her skin would be glowing from the amount of times she came. 

Y/N turned her head to the side, the sounds of soft breathing alerting her to the fact that she wasn’t alone. Dean lay on his side, one hand under the pillow supporting his head while the other was rested on top of the cover. She took a moment to truly look at him, she wanted to remember every tiny detail of his face. The way his freckles were lightly dusted across his cheeks and shoulders, the small crinkles in the corner of his eyes, the tattoo that was etched onto his chest. She lifted her fingers and slightly traced the outline of the ink, her fingers tingling at the contact. She so desperately wanted to remember everything about this moment, about him for she knew he would soon be a happy memory she’d escape to when times got tough. 

With a soft sigh, she moved herself away from the eldest Winchester, pulling the covers back and placing her bare feet on the floor. Naked, she padded along the floor, wanting to make herself look presentable before Dean woke up, wanting to be showered with a full face of makeup. As she walked, her fingertips ran along the edge of her dresser. She stopped in front of the drawers, her stomach churning as she did so. She knew she had to check in with The Master before she did anything. After what happened last night, after what Duke had said to her, she knew she was already in trouble. She just didn’t know how much. Quietly, she pulled the drawer open, fumbling around for her phone. When she retrieved it, she silently made her way to the bathroom, glancing over at Dean before she closed the door behind her. 

Holding down the power button on the phone, she reached into the shower and turned it on, hoping the sound of the water would help drown out her conversation. She sat herself down on the side of the bath, the phone in her hand as it began to violently vibrate. Notifications of text messages and missed calls. All from  _him._ She scanned over the texts. The first ones asking for a report, the ones after were telling her to be in contact as soon as possible and the last few were threatening. With a shaky hand, she opened the contacts and pressed call on the only number that was in the phone book. 

M. 

Hesitantly, she brought the phone to her ear. Her stomach churned, her mouth dry as she swallowed thickly. Her eyes were squeezed tightly shut as she awaited the inevitable. She didn’t have to wait long. 

“Y/N, Y/N, Y/N.” His voice made her skin crawl as he clicked his tongue against his teeth, he’d picked up the phone after the first ring. “You’ve been a bad,  _bad_ girl,” he drawled, a sinister tone to his voice. 

“Sir, please, let me explain,” she flustered, her hand coming up to rub at her brow. 

“No,” he snapped, “I’ll explain. You’ve lost me money. You’ve lost me credibility. You’ve made me look like a fool to one of our prestigious clients,” The master continued, his voice dangerously calm. 

“Mast-” 

“DON’T interrupt me, girl,” he snarled. “You were meant to be with Mr Orwig so imagine my surprise when I find out that you’re instead with Mr Winchester. I know what circles he runs in, he’s bad for my business, Y/N.” Fear flooded her veins. How could he not know where she was? It made no sense. A low chuckle bled from The Masters lips and she could picture his malicious smile perfectly. “Oh, baby, am  _I_ mad with you and to put the icing on this fruity little cake, my second in command comes here beaten and bloody.”

“But, Sir,” she panicked, her words fumbling from her lips as she tried her hardest to piece together her explanation. She knew Dean shouldn’t have attacked Duke, she knew how it would be all her fault and here she was proven right. But if she could just explain how Balthazar was the one who made this deal, who forced her into Dean’s hands then maybe, just maybe, The Master would be more lenient with her. 

“Oh, I’m not finished Y/N, I’ve not even started on you yet,” he growled, not allowing her to finish any of her sentences, “but I will, soon enough.”

“All of this is wrong, Sir, please,” she begged, her eyes burning with unshed tears. Her hand wound tightly in her hair as she desperately tried to turn this situation around. 

“I’ll see you soon, Y/N,” he sang down the phone before his voice became laced with anger once more, “I  _can’t_ wait.” 

With the phone still to her ear, silence engulfed her as The Master ended the call. She couldn’t move, she was finding it hard to breathe and the familiar feeling of terror washed over her. She knew what would be waiting for her back at The Hemlock. She knew exactly what The Master would have planned for her, the tone in his voice giving everything away. 

“Y/N?” 

The sound of her name being called made her jump, her panicked thoughts forgotten as the low rumble of Dean’s voice echoed from behind the bathroom door. She stood frantically, the phone clutched tightly in her hand as she looked around the room, desperate for a place to hide it. 

“Y/N?” he called once again, his voice sounding a lot closer than it did before. She could make out the thud of his footsteps and she knew he was just behind the door. One last look around the room, she slid the phone underneath a stack of towels on the shelves, turning it off as she did so. She knew if Dean caught her with this phone, he’d wonder why on earth she was hiding it. He’d think she was a spy or maybe double crossing him. If he found out it was because The Master liked to check in, he’d ask too many questions which would lead to more trouble for her.

With her hand tucked under the soft cotton towels, she heard the bathroom door open. Quickly pulling back, she spun to see Dean standing there in all his naked glory. One hand still resting on the door knob, the other by his side as his hungry eyes slowly took in the sight in front of him. Y/N had to try and quell the nerves that bubbled inside of her, her head slightly bowed in submission but her eyes continued to stare his way. 

“Now isn’t that the most perfect sight to see in the morning,” he spoke gruffly, a warm smile resting on his lips as his eyes raked over her body. She suddenly became very aware that she was naked, her hand coming to rub the side of her arm as they crossed across her chest. 

“I was just about to shower,” she explained, turning around to the gesture to the running water behind the clear glass doors. 

“Don’t let me stop you,” he said as he slowly stalked to her from across the room. She couldn’t help the small smile that graced her own features as he slipped his warm hands around her waist. His fingers gently pressed into her hips, his head dipping slightly as he ghosted his lips over the pulse point of her neck. Her nerves were slowly fading, the man in front of her taking away all of her fear and anxiety without even realising it. 

Allowing herself to breathe, she moved her head to the side, allowing Dean more access to her neck. An action that he responded to immediately. She slid her hands over his biceps, her featherlight touch making him grip onto her harder. He traced his tongue up to below her jawline, replacing it with soft kisses that travelled along until he found her lips, capturing them in a mind-blowing kiss. She couldn’t help the little whimper she made causing Dean to smile against her mouth. He pulled back, resting his forehead against hers, his arms now fully wrapped around her body.

“You broke the contract,” he whispered, his nose brushing hers as he smiled smugly. However, the statement made Y/N pull back slightly, an amused expression on her face as her hands rested on his bare chest.  

“Excuse me?” she asked playfully, her eyebrows arched as Dean continued to smile down at her, his hands still held tightly around her waist. 

“ _You_ kissed me,” he reminded her, his smug grin widening but Y/N just shook her head. 

“The contract said no sex Dean, not no kissing,” she teased as she worked her way from his arms, “remind me, who was it that pulled me in to feel their boner?” With a knowing smile, she sauntered over to the shower where she slowly slid open the glass door, leaving it ajar. She knew he was watching her every move, how she stepped under the spray and caressed her own body. It wasn’t long before she felt his chest pressed hard against her back, his fingertips tracing the curve of her hips. 

“You groped me,” he husked, his fingertips pressing hard around her waist as he pulled her ass into him. 

“You undressed me,” Y/N countered, a small gasp bleeding from her lips when she felt his very obvious arousal as his stubble grazed over the curve of her neck, his hot breath fanning over her ear.

“You undressed me first.” His lips pressed softly just behind her ear before she turned in his arms, pushing him back slightly as she stepped out from under the perfect pressure of the running water. She slowly let her eyes travel the length of his body, appreciating all of him as he stood there, his body glistening wet. She couldn’t help but feel the ache between her legs when she saw how hard he was for her. The way he stood there, his eyes blown with lust as he took all of her in. This feeling was fresh, it was new and it was most certainly exciting. 

"I think you’ll find that you did most of your undressing yourself. For the most part,” she teased, leaning back against the tiled wall as she held his gaze. She’d never been so sexually attracted to one of her clients in the six years she had been working.  _She loved it._

She allowed her fingers to slowly trace her skin, down from her neck to her breasts, her fingers working her own nipples as she held Dean’s gaze. His fingers balled into fists at his sides as he watched her, his tongue peeking out over his bottom lip to draw it between his teeth as his eyes stayed focused on hers. Her fingers continued their descent on her body, her nails ghosting over her navel before one of her hands slid between her legs, her fingers starting to work on her small bundle of nerves. She couldn’t help the small gasp that left her lips, that being the only noise that echoed through the room along with the sound of the pressured shower. She watched him through the mist of the spray, beads of water dripping from the end of his nose as he continued to watch her. She noticed how one of his hands had started to pump himself, working his long, thick cock in his palm to the show in front of him, but it wasn’t enough. 

“C‘mere,” he growled, reaching for her through the falling water before pulling her into his arms. She had no time to react before his lips were on hers, desperate and hungry. His tongue traced her bottom lip, begging for entry. She mewled against him, opening her mouth to allow him to deepen the kiss before she felt the coolness of the tiles beneath her back once more. A gasp left her lips, the weight of his body on hers was delectable, his arms caging her body in as his kisses grew more hungry. 

She allowed her hands to wander, her fingertips gliding down his wet skin before her palm wrapped around his length. She began to work him, low moans emitting from his mouth as he broke away from her lips, his kisses travelling down her neck as his hand came to rest between her legs. He encouraged her to open them wider, allowing his fingers to dip into her folds with ease and he let out a low growl when he felt how wet she was for him. She whimpered at his touch, the way his fingers were working her clit was enough to make her legs begin to shake. The way he then slid them down through her folds to enter her made her scream, he’d only had her body for one night and he already knew exactly how to press all the right buttons. 

She began to pump him harder, closing her eyes to concentrate on the feeling of euphoria that was washing over her. His free hand was kneading her breast, his thumb tracing over her nipple as his mouth continued his pleasurable assault on the skin of her shoulder. She felt the coil in her stomach tightening, her pussy clenching around his fingers as Dean worked her closer to ecstasy. With a flick of his thumb over her clit, his other hand continuing to knead her breast, she was a goner. Burying her face in his neck, the coil snapped and she moaned against his wet skin as he slowly brought her down from her high. She wanted to return the favour. She was desperate to feel the weight of him on her tongue once more, having him growl her name as she took him deep in her throat and so, she began to sink down to her knees only to have his large hands stop her. 

“Not now, sweetheart. Need to feel you,” he told her, his voice low as he guided her back against the wall, his hands hooking underneath her thighs. Y/N didn’t have time to protest as he hoisted her off the floor, her legs instinctively wrapping tightly around his middle as she gripped onto his shoulders.

She felt him already nudging at her entrance, but he waited, his focus on the searing kisses he was giving her instead. He was teasing her, she knew that and the way she attempted to buck her hips against him made him smile into the kiss. She was at his mercy, his arms hooked under her legs, his weight pinning her against the wall and his cock just throbbing at her entrance. She’d never wanted someone more.  

He soon gave in to Y/N’s whimpering pleas, lining himself up perfectly with her entrance before he slowly filled her, the feeling of him stretching her erupting goosebumps across her skin. He’d bottomed out inside of her, filling her wonderfully and all she could do was clench around him. She needed him to move and the roll of her hips told him that. He moaned low against her lips before he withdrew from her, only to enter her again with a steady force. His breath was ragged as he thrusted into her, his pace picking up slightly causing her to grip onto him harder, her lips biting and nipping at his neck. He moaned her name, his fingertips digging hard into her thighs as he continued to fuck her against the tiled wall. She wanted to throw her head back but it had nowhere to go. Instead, she dug her fingernails into the nape of his neck, her screams echoing around the bathroom. 

She felt her stomach tighten once more, the coil within her ready to snap as Dean worked her body like he’d known her for years. It didn’t take long for his hips to stutter, his rhythmic thrusting to lose it’s pattern as he chased his delirium. His green eyes snapped to hers, holding a gaze so intent that it made her stomach flip. She studied the crease in his brow as he concentrated; the corner of his lip he was biting as he held back a moan. Her mouth hung slightly agape, allowing the breathless whimpers to pass her lips. Her toes curled slightly, her legs tightened around his waist as she rolled her hips in time with his. Her coil snapped, her orgasm washing over her like a pleasurable tidal wave and she relished every minute of it as she clung tightly to Dean. He helped her ride it out, his end not far behind hers as he coated her insides with everything that he had. 

Breathless, they both took the time to recover. Neither of them wanting to admit to the other how different it felt compared to all the other encounters they’d had before. Y/N held Dean close as he rested his forehead against her shoulder, she was trying to focus on the way she could feel his heart beating through his chest onto her skin. The way he felt held tightly against her body. This was something she wanted to remember for a long time. Not because of how insanely hot it was, nor how the orgasm was one of the best she’d had; she wanted to remember it because it felt new and different. It felt passionate. 

Lifting his head, he placed a soft kiss on her collarbone before he placed another one to her cheek. He slowly withdrew from her, letting her down so her feet were feeling the warm tiles beneath her. She shakily stood, her hands sliding down his chest as she tried to compose herself. No words were spoken between them in that moment, they didn’t have to be. Instead, he reached to the side of her for her shampoo and began to wash her hair, allowing his fingers to massage her scalp before he guided her back under the spray of warm water to rinse. 

Her heart was still beating fast within her chest, her stomach was still doing somersaults as he continued to look after her. This was something she’d never experienced before. Normally, her clients had their fill and moved on but Dean, he was different. He was washing every inch of her like she was the most delicate thing on earth. 

Once he was satisfied that they were both clean, he turned off the shower before he reached out for a towel from the shelf, Y/N’s eyes widening slightly when she remembered what was buried beneath. But Dean only took two, leaving the phone safely hidden. After wrapping one around his waist, he walked back over to Y/N with a towel open wide. He wrapped her in it softly, placing a gentle kiss to the top of her head before he scooped her up in his arms. She squealed slightly at the unexpected movement but that sound was swallowed by his lips when he lovingly kissed her once more as he made his way back to her bedroom. 

–

Y/N rested her head against his chest, her smile wide as she listened to his heartbeat calming down for the second time that morning. He closed her eyes and tried to focus on the feeling of his calloused fingertips slowly tracing the length of her back, the feeling making her sleepy. In this split second, she felt content, she felt happy but as soon as that feeling came, it was taken away by the reality of the situation. He was her client, nothing more and she had a job to do. 

“So, as much as I’d love to stay here like this all day, you’ve got work to do,” she sighed, patting his bare chest lovingly before rolling away from him, taking the cotton sheet with her to cover herself. She saw how Dean looked at her, leaning over onto one elbow as he began to process his thoughts. 

“I do?” he asked, confused. His brows had knitted together and Y/N could almost see the cogs turning in his mind. She tucked some of her hair behind her ear as she smiled down fondly at him.

“You’ve got a meeting with Abaddon later this afternoon, remember?” she prompted as she stood from the bed. Dean silently nodded in agreement as he watched her move, the cotton sheet she clung to covering her modesty as she walked to her dresser. 

“What about you?” he asked as he sat further up in her bed, his green eyes not once leaving her figure. Y/N sighed softly before dropping her the sheet to the floor, stepping gracefully into the black lace panties she’d picked out. 

“Well…technically my purpose with you has been fulfilled. We’ve done the Gala, we’ve secured meetings, the Winchester’s are on the up again…” she explained as she pulled the matching black lace bra from the drawer. 

“Why do I sense a but coming?” Dean pulled one leg up and rested his arm on his knee. Y/N squeezed her eyes shut momentarily, her thoughts going back to The Master and her room back at The Hemlock. She was so desperate to not go back there but she had to be honest with Dean, he was her client after all. 

“…but I would like to make use of the time I have left here with you. I have three days to help finish what I started here. If that’s not what you’d like, you can send me back to The Hemlock,” she proposed even though her gaze was firmly fixed to the floor. She heard Dean shuffle across the bed before he was in front of her, his forefinger coming to hook under her chin as he tilted her head to look at him. 

“Oh, sweetheart, you’re definitely staying to finish what you’ve started,” he drawled, his lips coming down to capture hers in a heated kiss. One that made her reach out to hold onto him as his swollen lips encased her own. “But really, just three days left?” he whispered against her lips, his nose brushing delicately over hers. 

Y/N was finding it hard to gather her thoughts, her eyes trained on his mouth as he spoke. Her heart was fluttering in her chest, her stomach turning over with excitement as she tried to catch her breath. Before she could answer however, the sound of a strong vibration cut through the sexually charged silence. Like a bucket of cold water, Y/N backed away, forgetting for a moment that her phone was still buried under the towels in the bathroom: switched off. Dean hadn’t seemed to notice the sudden change in her behavior as he looked over his shoulder to the nightstand where his phone was lighting up. Reluctantly, he pulled away and made his way over to answer the call. As he looked down at the screen, a small smile appeared on his lips before he brought the phone to his ear. 

“Hiya, Sammy,” he sang, looking around the floor for his boxers as he placed his phone on loudspeaker. 

“Dude, where  _are_  you?” Sam questioned, sounding a little frustrated. Dean looked over at Y/N and allowed his smile to widen into a grin as he pulled his boxers up his thick bow legs. 

“Paradise, little bro, paradise.” Dean sent a wink her way as he heard Sam scoff down the phone. Once his boxers were secured around his waist, he took the phone off of speaker and nestled it next to his ear. “What’s up?” Dean asked, continuing the conversation as he began to walk the lengths of Y/N’s room.   

She couldn’t help but watch him as he easily strode back and forth, his hand coming up to rub at his forehead as he concentrated on what his brother had to say. As she took a moment to herself, Y/N allowed a natural smile to form on her lips.  _He wanted her to stay._ Sure, it was only for three more days but to her, that meant everything. For three more days she was safe, away from The Master, away from Duke and away from The Hemlock. It made her happy to know that Dean was enjoying her company that much that he wanted her to stick around. She hoped that if he gave a good report at the end of her contract, The Master would be a little less harsh on her. A girl could only hope. 

She moved around her room and gathered her clothes for the day, a pair of dark fitted jeans matched with a loose fitted black blouse. Considering she was staying in the Winchester Manor today, she knew formal attire wouldn’t be entirely necessary but she still wanted to look presentable all the same. She wanted to make the most out of the three days she had left, she wanted to enjoy what little time she has left with Dean and the rest of his family. He was a welcomed break to the clients she’d dealt with before, she felt more at home here than she ever had anywhere else. She was determined to put her best foot forward and try to block The Master from her thoughts, if she didn’t, she’d send herself mad just thinking of what punishment was awaiting her. 

“Alright, I’ll be down in a minute,” Dean sighed, ending the call and throwing his phone on top of the bed before running both hands down his face, rubbing at the stubble on his chin. Y/N delicately stepped into her jeans, slowly pulling them up her legs as she glanced back over at the eldest Winchester. 

“Urgent business?” she questioned, trying not to sound too defeated that he’d be leaving her company so soon. Dean just nodded, reaching behind his head to scratch at the back of his neck. His actions made her arch her brow, her stomach turning over when she realises that Sam may know what had happened between them. “Does he know about…”

“Most probably,” he confirmed, nodding slightly as he looked around for more of his clothes but it was to no avail, he knew exactly where his clothes were, a thought to which he smiled. “If he’s been into my office then…most definitely,” he beamed but Y/N only gave him a small smile in return.

“He’s not going to be very happy with me, is he?” she asked softly. She knew that Sam wasn’t her biggest fan to begin with and he definitely wasn’t on board with the idea of hiring her. So the fact that they had now gone and broken the contract Sam had spent hours working on was just going to make matters ten times worse. However, Dean just frowned as he looked Y/N’s way.

“Why?” he prompted, her question lost on him as he tried to understand where she was coming from. As Y/N pulled her blouse over her arms, she gave him a deadpanned look before nodding towards her messed up bed as she began to do up her buttons. Dean’s eyebrows suddenly rose in realisation before his signature grin was back. “Sweetheart, you leave my little brother to me. You’ve got nothing to worry about,” he assured her before he grabbed his phone and walked over to her. He rubbed at the tops of her arms gently before placing a soft kiss on her forehead. He pulled back and started to walk towards her bedroom door, his hand barely touching the handle of the door before Y/N turned around to stop him.

“Dean?” she asks gently, “about my time left here-” 

“What do you need?” Dean’s features were soft as he looked at her and her lips twitched at how he knew exactly what she was going to ask. She wrung her hands together in front of her as she walked slowly over to him by the door, her Y/E/C eyes locked onto his. She knew exactly what she wanted to do with the time she had left and she could only hope that he would approve of her intentions. 

“Information, mainly. Dean, I want to help you find out who killed your parents. After being at the Gala, seeing how everyone acted around you…I don’t know. Something seems off,” she began to explain, her hands still clasped together in front of her as she stared up into his green eyes, “If you’ll let me help, then I’m going to need to look over some old documents. I’ll need access to some of your files as well as a more efficient work space than here,” she continued, nerves lacing her tone as she laid out her proposal. Dean pulled back slightly, his tongue coming to trace his bottom lip as he thought her plan over. Y/N realised in that moment that it was a big ask considering he’d had people screw him over for his information before. Internally, she began to panic. What if she had just ruined everything in that split moment? What if he thought she was a spy? 

“You can work in my office,” he told her, opening her bedroom door before he stepped out into the hallway. It took a moment for his answer to sink in and a wave of relief washed over her when she realised that he trusted her. 

“R-really?” she stuttered mildly, a little bit of disbelief in her voice. Dean just nodded once more as he motioned for her to follow him down the hall as he walked. 

“I’ll rope Sammy into helping you. He’s one of the best when it comes to research and then after my meeting, I’ll come on board too,” he explained, his arm coming to rest around her shoulders as he guided her back to the place where they both gave into each other the previous night. 

“Sounds like a plan,” she agreed, allowing her arm to come up and wrap around Dean’s middle to ensure he stayed close to her side. Without realising it, he’d given her a new lease of life. She felt as though she was part of something and she wanted to thank Dean for everything he’d done for her so far. What better way to do that than to find the assassin that murdered his parents.


	19. Chapter Seventeen

**Notes for the Chapter:**

> Sorry guys that this took so long...again. 
> 
> Christmas, a one year old, husband and work...I don't even know where my December has gone! I had two days off for the holidays from work and any spare time I found, I was chipping away at this add...but here we are. End of 2019 and a new add for Life for Rent. 
> 
> Hope you lovelies enjoy it when you get to read this! Hope you've all had an amazing Christmas and your New Years will be a fun one! 
> 
> Stay safe, much love!   
> xox

Dean’s bare feet padded along the carpeted hallways as he headed towards his bedroom, wanting to at least throw some clothes on before he headed downstairs to meet his brother. No matter how hard he tried, he couldn’t wipe the smile that graced his lips each and every time he thought of his intimate encounters with Y/N. She’d been better than he thought she would be, she’d beaten his imaginary fantasies of her hands down and he felt elated. The thought had crossed his mind that it could have only felt that good because he had gone without sex for a long period of time but that was ruled out this morning when he’d had her once more against the wall of the shower. 

His thoughts then progressed onto her proposal of helping him to identify the assassin that had murdered his parents. It was a long shot, he knew that. He’d spent months trying to work it out, going over police reports, threatening the low members of other rivals to spill information but it had got him nowhere. He still hadn’t made peace with their death, how could he? They were taken quickly and aggressively. However, the thought that Y/N actually wanted to lend a hand to try and help, gave him a slither of new hope. Fresh eyes scanning over what little evidence they had tied in with her set of skills could actually get them somewhere. He was dubious at first to let down his guard and allow her to work in his office; alone. There were many documents in there that were private, documents that held family secrets and fortunes. Locations of bunkers and hideouts in case anything ever went awry. But then he remembered something his Mother had told him long ago;  _trust with your heart, lead with your head and go with your gut._ He only had to look down into Y/N’s eyes to see that she truly wanted to help him and so he was trusting with his heart.

After getting dressed into something more comfortable, a grey Henley and matching sweats, Dean had made his way towards the kitchen where he knew Sam would be waiting for him. The smell of crisp bacon and fresh coffee delighted his senses as he entered the room, a soft smile being sent in Magda’s direction as she automatically began to plate him his breakfast. Pouring himself a fresh coffee, he looked over to see Sam sitting at the dining table staring at his laptop. Grateful, Dean took his plate from Magda and made his way to join his little brother. 

“What’s so urgent, Sammy?” Dean asked, not bothering with a greeting as he set down his plate. Pulling the chair out from under the table, his green eyes bore down onto Sam as he waited for him to respond. The youngest Winchester rose his eyebrows before sliding his open laptop towards Dean, an open document ready for him to read. 

“Dean, we’ve had three upcoming mobs surrender to our services overnight. They’ve sworn loyalty to us,” Sam explained, one of his large hands gesturing towards his screen whilst the other used his fork to poke around at his egg white omelette.  

“You’ve got to be shittin’ me,” Dean astonished, mouth full of bacon as he pulled Sams laptop closer to him to check his eyes weren’t deceiving him, “Is this a set up?”

Sam just shook his head as he shrugged his shoulders. “Not as far as we can tell. We’re taking the necessary steps to ensure that they  _are_  loyal and so far, so good.” Sam leaned over to his laptop, using his fingers to trace the track pad to move the document down, showing Dean the rest of the file. “They’re signing these contracts today,” he continued, a smile on his face. Dean pursed his lips and nodded, bringing another rasher of bacon to his lips as he pushed the laptop back towards his brother. 

“Why the sudden surrender?” he asked, curious as he chewed down on his breakfast. 

“They were impressed by your show of leadership last night at the Gala. Not only that, a few of them weren’t so impressed with Nick’s show of things,” Sam explained as he took his final few bites of his omelette, using a napkin to dab the corners of his mouth. Dean allowed a smile to tug at the corner of his lips, his mind briefly going back to how his morning started only to be improved by this news. 

“Well, my morning keeps getting better,” Dean sang, wiping his hands down his sweatpants before reaching for his coffee cup, bringing it to his lips as he winked at his little brother who was frowning at him. 

“Why? What else has happe-” Dean’s shit eating grin stopped Sam’s question in its tracks, an unimpressed look resting in the youngest Winchester’s features. “You slept with Y/N didn’t you?” 

“Don’t give me that look, she broke the contract,  _she_  came onto me,” Dean boasted, licking at his top lip as he placed his cup back on the table.

“…and I’m sure you did everything in your power to stop her,” Sam remarked, slightly shaking his head.

“She’s a very strong willed lady, Sammy.  _Very_  hard to say no too,” Dean continued, his smile never fading. 

“I’m sure.” Sam rolled his eyes as he reached for his coffee next to his plate, taking a long sip. 

“Anyway, I’ve got a job for you,” Dean announced, ticking his jaw slightly as he looked down at his plate. He wasn’t sure how Sam would take his request. 

“Do you not think I have enough work already?” Sam sighed, placing both of his hands on his thighs as he frowned towards his big brother. Dean took a deep breath, his earlier smile had faded from his lips and his look became one of importance. 

“It’s to do with mom and dad,” he spoke softly as he watched Sam’s eyebrows shoot to his hairline, “Y/N wants to help us find out who killed them,” he continued, his green eyes boring into Sam’s as he waited for his reaction. 

“How, exactly?” Sam questioned, his brow creasing into a soft frown as he tried to take it all in. Dean could see the wheels turning in Sam’s head, thinking over everything they’d already been through and gone over but had come up with nothing. 

“Research, fresh eyes going over what little we’ve got already. I told her you’d go and help her, considering you’re the best at that sort of thing. I’ve left her in the office,” Dean said quickly, leaving little room for Sam to contest it but he saw how his little brother’s expression quickly turned to one of disapproval. 

“With all of our documents? Dean-” 

“I trust her, alright?” Dean interrupted, his tone a little sharper than necessary. However, he knew Sam had a point due to his carelessness with women in the past. “Besides, we can get Charlie or Kevin to remote access her laptop to see what she’s been up to and delete any files she has,  _if_  she has any,” he clarified, hoping to ease Sam’s worries a little as well as convincing himself that he was doing the right thing. “Once my meeting with Abaddon is over, i’ll come and join you,” he added before going to finish off his breakfast.

“Fine,” Sam huffed, closing the lid of his laptop as he stood before he tucked it under his arm. With a small sigh, he picked up his half empty coffee cup and began to make his way towards Dean’s office. 

“Play nice, Sammy,” Dean warned, a hint of playfulness in his tone as he watched Sam walk out of the dining room. 

Wiping his hands clean on his napkin, Dean leaned back into his chair as his hand cradled the half empty cup of coffee on the table, absentmindedly running his thumb along the rim as his mind began to wander. Sam had a right to be a little upset with him, he knew that. Dean’s list of mistakes since their parents had been killed had been one too many for his little brother, the last one involving Cassie being the final straw. His relationship with Sam had been strained since then, only recently did he feel like he was beginning to get his brother back. Sam had seen a change in him in the recent weeks, he knew that. Dean’s focus had returned, his determination to protect his family; to honour the Winchester name. It was all back. He’d like to think to think that it was because he woke up to the realization of the shit storm his family were in himself, but in actual fact he knew it was all down to the woman who was currently sat in his office trying to help identify the person who sought to bring down his family’s empire to begin with. 

He got to wondering whether he could trust Y/N with everything and anything about their family business. He’d had his fingers burned too many times from women who had whispered sweet nothings in his ear only to hold a sharp knife to his back, metaphorically of course. His heart was telling him that she was different, that he could trust her but his head was telling him to tread cautiously; his gut hinting to him that there was more that what appeared to be. When he awoke that morning to an empty bed, his heart began to race, his head thinking the worst had happened but when he had time to focus and he heard the shower running, his panic subsided slightly. But something was bothering him; he thought he could hear her talking to someone which prompted him to call out her name. When she didn’t answer, he grew more concerned and called again, walking faster towards the bathroom. But as he opened the door, he was greeted with Y/N standing there naked, her head bowed slightly as if she was awaiting a command. His defenses lowered slightly at the sight of her, the thought of her talking pushed to the back of his mind until now. 

As he replayed the morning over and over in his head, he could only come to the conclusion that she could have been singing or maybe even talking to herself. The only way he’d know for sure would be to ask her outright, something he planned on doing later that evening. 

–

Taking a deep breath, Y/N bit back a smile as she looked around Dean’s office. Scattered clothing littered the room from the night before. Her dress was still in a puddle on the floor, his shirt strewn across the couch alongside his trousers. She made her way around to the front of his desk only to find her panties and bra laying at the feet of his chair. It would be a moment she would relive in her head over and over again. However the thought of Sam joining her at some point soon spurred her into cleaning the discarded clothing away. She folded Dean’s shirt and trousers neatly, placing them on his chair as she was unaware of where else to put them. In regards to her underwear and dress, she quickly bundled them together and hastily made her way back to her room. She neatly hung her dress on the bathroom door frame, throwing her used panties and bra in her suitcase before grabbing her laptop and notepad as she headed back towards Dean’s office. 

Y/N didn’t really know where to start as she placed her laptop down on Dean’s desk. She didn’t want to go searching through his cabinets and drawers for files, understanding that the Winchesters previously had issues with women with wandering hands, so she thought it would be best to wait for Sam. Instead, she grabbed hold of a whiteboard that appeared to be on wheels and moved it towards the edge of the couch, deciding on making a mind map of everything she already knew about the assassination of Mary and John Winchester. She needed to visualise everything in one go and hopefully, with the help of the brothers, they may be able to find a lead or clue that might have been missed before.

It didn’t take Y/N long to print off local reports and photos of the Winchester case. After a brief internet search she found a few items that could prove useful, key details such as time and cause of death, location, vehicle make and model; she didn’t want to miss any tiny detail. She then pinned what information she had onto the board and started to link existing facts together. As she stood back and looked over what she’d accomplished already, she knew there had to be more to this than what meets the eye; that much was clearly obvious. Y/N was that engrossed in her research, making notes on her laptop, that she didn’t hear the office door opening behind her.

“Wow, that’s impressive.” The compliment made her jump in her seat, her hair swishing around her face as she spun in the direction of the voice. Standing there, coffee in one hand and his closed laptop topped with files in another, was Sam Winchester. His expression was hard to read, his eyebrows were slightly raised as he stared towards the board Y/N had created. 

“Oh, h-hey Sam,” she stuttered slightly, feeling nervous suddenly at his presence. Something that Sam picked up on as he walked towards her, placing his coffee down onto the table. 

“You alright?” he asked, glancing briefly up at her in concern.  

“Yeah, sorry I just didn’t hear you come in,” she replied honestly, a small smile on her lips as she tucked her hair back behind her ear before focusing back on her laptop. The silence that fell over them was somewhat awkward. Y/N didn’t know what to say next, her mouth slightly agape as she coyly looked over to him as he settled down across from her. Sam was paying her no mind as he opened his laptop and took a small sip from his coffee cup. She knew she had to say something, anything to break the quiet that was engulfing them. Clearing her throat, she straightened her back in her seat, wringing her hands together as she did so.

“So, I don’t know where you want to start but I kind of just found everything I had already and put it on here so I could visualise it better,” she started, gesturing to the board and the few notes next to her laptop on the table. She took a chance to look over at Sam, who held a tight smile on his lips. 

“That’s good, Y/N. I’ve been over and over this information so many times…” he sighed, sounding slightly defeated as he ran one of his hands through his long hair. She saw the pain that was sitting behind his eyes as he looked over at the board; she knew that this was going to be incredibly difficult for the pair of them to go through. “Dean said we needed to give our parents case a pair of fresh so…here,” he spoke softly as he handed her a large brown envelope that was already open. Y/N took it gently from him, using her fingers to cautiously widen the open end to place her hand inside. “In there is all of the crime scene photographs. I say we start there,” Sam suggested, giving Y/N another tight smile before looking back down at his laptop. 

“Ok,” she agreed, her fingers tracing the edges of the photographs when Sam’s voice sounded once again.

“How do you know how to do any of this stuff anyway? Like what experience do you have of crime scenes and investigation?” he shot out, his eyes boring into hers as he awaited her answer. Y/N was taken aback, naturally, by his sudden outburst and the evidence of that was written in her facial expression. One Sam quickly picked up on. “Sorry, that came across extremely dickish. It’s just with your… _line_ of work, I wouldn’t have thought that this stuff would be near your radar,” he spoke a little softer, an apologetic smile being sent her way as he awaited her answer. 

“It wasn’t, for a while. I know you think that all I do for a living is open my legs and flirt my way into anyone’s good graces but…believe me, I wanted to be more than that, I still do,” she spoke softly and honestly. She had to ensure that he could trust her, trust that she’s not doing this for any other reason than to help them. “My clients aren’t all the same. Some are dodgy captains for the Feds, some are senators around the world; others are just like you and Dean. To ensure I survived in this world, I needed to adapt, I needed to learn from those around me. So whilst I was working for my client who was a Fed, I learned a thing or two. I read books, reports, watched and took in whatever I could. Learning a new skill is just another arrow in my quiver,” she explained, her words true as she stared back at Sam to judge his reaction. It wasn’t her entire truth, no one could know that but it was truth enough to hopefully convince the youngest Winchester that she could help in someway.

“Fair enough.”

After that simple response, an unusual silence fell over them, one that wasn’t uncomfortable but one that wasn’t too comfortable either as she began to pull out the crime scene photographs and place them next to each other on the table. She swallowed hard when she pulled out the picture of Mary and John, deceased in the front of their vehicle, bullet wounds to their heads. There were close ups of the injuries, photos of the car that was found surrounded by trees and other greenery. There was a photo of a boot print that had been left in the mud, tyre tracks from the highway the Winchester parents were travelling along. Once Y/N had placed all the photos onto the table, she glanced another look up at Sam who was avoiding looking at the evidence in front of him, choosing to instead sip at his coffee and stare at his laptop screen instead of the table. 

Y/N took a deep breath and exhaled it out slowly from her mouth. From the beginning, she knew Sam hadn’t been given the greatest impression of her, even after what she’d done for the business so far; he was still very much guarded. She could understand that after Dean’s past discretions and after last night; with everything that happened with Duke causing a scene and then her intimate evening with his older brother, she knew she’d only gone and proved Sam’s obvious opinion about her right. Closing her eyes and taking another deep breath, she knew she had to clear the air somehow if they were going to work on this sensitive case together. 

“Sam, about last night…” she started, her voice quiet as she stared down at the table. Sam let out a soft blow of air through his nose, his fingers coming to a halt from typing on his keyboard as he looked up at her. 

“Y/N, you don’t need to explain anything to me,” he told her, a much more gentle look resting on his features than what was there a couple of minutes ago. 

Y/N frowned, “but-”

“But what?” Sam interrupted, taking in the confused look on your face. “Look, as much as it pains me to admit it, Dean was right in hiring you. He’s been a little less reckless whilst you’ve been helping him and I can only see that as a good thing,” he explained, sending Y/N a soft smile. “Plus from what I hear, that Duke guy deserved what happened to him,” he continued, offering her a reassuring look before he once again picked up his coffee. 

“So you’re not mad?” she asked after a few moments had passed. A moment ago, he was more than just a little passive aggressive with her and now he’s telling her he’s all good. She didn’t know what to think so the question was one that needed to be asked. 

“Why would I be mad?” he countered back, not bothering to look up from his cup as he took another sip.

“The scene that was caused. The kiss me and Dean shared, what we did; it states in the contract that it should only be for show purposes. We broke that,” she admitted honestly, a lump forming in the back of her throat when she thought about how much trouble she was going to be in when she got back to The Hemlock. The words of her Master echoing through her mind. If Sam were to file a complaint on top of all of that, she wasn’t sure she’d be back in action anytime soon. 

“You did, but do you really think I wouldn’t have created a few little loopholes here and there?” Sam chuckled as she shook his head, placing his now empty coffee cup back on the table. “Trust me, I know my brother too well to not make sure there’s a plan B.  Let me worry about the contract, you just worry about trying to make sense of all of this.” He gestured to the table full of evidence that had been gathered already as he stood from his seat, leaning across to place a comforting hand on her shoulder, “we’re good, Y/N.”

“Thanks, Sam,” she replied softly, her hand gently patting his as he gave her one last squeeze before sitting back down to his computer. 

Hearing those two words,  _we’re good,_ meant a lot to her in so many ways. First and foremost, it meant that she could get through this task without feeling like there was a weight on her chest, holding her down. Secondly, she felt somewhat accepted by Sam and that meant a lot considering they’d hardly spoken. Yes, he was skeptical of her but that was to be expected considering circumstances. It also made her happy that she’d had an effect on Dean just like he’d had an effect on her. She was glad he wasn’t being as reckless anymore, he was smart and calculated but his grief had pulled him down. She was just happy he was back on the right path. Then thirdly…thirdly it meant that Sam wouldn’t be reporting any complaints back to The Master. So, with a smile on her lips and her head in the right place, she focused on all the material she had in front of her, determined to find a lead before her days were up at the Winchester Manor. 

-

Relaxing into the leather of the backseat of the Range Rover, Dean had a wide smile on his face. The meeting with Abaddon had gone well enough that a truce had been forged and a deal made. Abaddon had made it clear from the beginning that Dean wasn’t her favourite person out there and under any other circumstances, she wouldn’t be so forthcoming in agreeing to her truce but her hatred for Nick outweighed her hatred for Dean. Everything was going according to his plan, the Winchester’s were gaining more respect and alliances daily, they were climbing the ranks once more and it was all thanks to Y/N. She somehow managed to make him drag his head from out of the gutter to focus on his family business instead of whiskey and women. He smiled when his thoughts travelled back to her; how determined she was to help him find his parents assassin. But his smile dampened when he thought of her leaving his life in three days time. 

As Garth pulled up in front of the house, Dean leant forward between the seats and patted him on the shoulder in thanks before he swiftly got out of the vehicle. He unbuttoned his suit jacket and placed on hand in his pocket as he ascended the stairs to the front door, eager to get back to his office; to get back to Y/N. He was looking forward to letting her and Sam know how the meeting had gone, that they now had Abaddon’s support going forward. For the first time in a long time, Dean could actually see the light at the end of the tunnel, he could see him and Sam standing where his father once stood at the annual Gala and he was going to let nothing stand in his way. As he turned the corner of the corridor, his eyes landed on his office door and his pace quickened slightly. His large hand rested on the door handle, pressing it down to uncatch before allowing it to open just a crack before an out of breath voice stopped him in his tracks. 

“Hey, Dean! Do you have a moment?” He turned to find Charlie catching up to him, her breathing rapid as she fanned herself. It was obvious that she’d rushed to catch him as soon as he arrived home and his eyebrows creased together slightly when he noticed the folder she was holding in her hand. 

“Sure, go ahead,” he encouraged, his hand still on the handle; the door still ajar. Charlie peered to the side and noticed the opening, her smile dwindling slightly.

“I really need to speak to you in private,” she urged, nodding her head down the corridor towards the boardroom. Dean’s frown deepened which caused Charlie to let out a big sigh, her eyes widening slightly. “It’s in regards to that matter you asked me to look into,” she all but whispered, trying to use her wide eyes to convey the meaning behind her words as she stared him down. 

Dean’s frown slowly disappeared, realisation washing over him as he nodded and gestured for Charlie to lead the way. He closed the door and followed her, his mind running at a million miles an hour. He’d been so swept up in the success of his mob rising through the ranks once more, enveloped by the whirlwind of the past twenty-four hours that he had briefly forgotten his early suspicions surrounding Y/N. The way she acted when they went shopping, her reaction to her dress, the incident at Pam’s Pizzeria and hearing her talk in the bathroom this morning; something was definitely up and the fact Charlie was eager to catch him with information made his blood run cold.

“You got something?” he asked as they entered the board room, hastily shutting the door behind him before he turned to face the redhead. Charlie nodded, holding out the brown folder in front of her and urged Dean to take it.

“You really need to see this.”


	20. Chapter Eighteen

“What’s in this, Charlie?” Dean voice was gruff as he took the brown folder from her encouraging hand, his eyes staring into hers as he waited for her response.

“You’re not gonna like it, that’s for sure,“ she told him, a small breath escaping her lips as she shook her head slightly. 

“Why?” Dean swallowed hard, his throat tightening as his mind reeled off as many different scenarios as it could muster. 

"Just look,” Charlie urged, her voice still soft as she gestured to the folder in his hand. He didn’t say another word, instead he clenched his jaw and cleared his throat as he opened the folder. His rough fingers slid over the edges of the files inside before he pulled them out, throwing the now empty folder onto the boardroom table in front of him; his eyes wildly flicking over every word on the pages before him.  Beside him, Charlie watched for a few moments, allowing her boss to take it all in before feeling the need to fill the silence with clarification, unsure as to whether Dean was truly seeing what she was trying to show him. 

“When you asked me to look into Y/N, originally I found nothing, her record was clean as you know. But to me it seemed  _too_ clean. No hospital appointments, no broken bones; no fines of any kind. The further I dug the more unrealistic it became. Straight A student, no bad marks against her name in any educational system and she’s not even registered to vote.“ 

"So she was a goody two shoes at school and hasn’t got any interest in politics, that’s hardly damning evidence, Charlie.” Dean was frustrated as he looked up from the documents to the redhead in front of him, feeling like there wasn’t a point to him looking through the pages in his hand. This was information he mainly knew,  he’d even suspected her of being a straight A student considering the talents Y/N held. 

“That’s what I thought until I found an irregularity in the coding. It confirmed my suspicions that someone could have fabricated Y/N’s records. So after  _a lot_  of time, code and even more encryptions, I managed to break through that digital barrier and…well I was right. Her entire record is a lie. What you have in your hand, that is the real Y/N." 

The tone in Charlie’s voice urged Dean to look back down at the documents in his hand, his green eyes scanning the pages much slower than they were before. Without taking his sight from the paper in his hand, he reached out in front of him for a chair, pulling it back and sitting down as he continued to read. He appreciated Charlie’s silence as he took in everything that was printed in black and white. Her birthday, the place she was born, her birth weight; her last name, Y/L/N. 

His fingers flicked over the page, there was an old address, the names of her parents and a sibling, the first school she attended as well as records of all of her shots from when she was a baby. The one similarity to the fake records was that she did get pretty good grades, not one teacher had a bad thing to say about her. That caused Dean’s frown to deepen, he knew he didn’t know much of her personal life and the more he thought about it, the more he realised he hardly knew anything. To him, that was understandable and not too much of an alarm call. She was private about her past, something he could relate to. He hadn’t exactly sat her down and asked for her origin story, word for word. 

Another page flick, another sheet of information. This document highlighting all of her doctors and hospital records from the age of two and up. She’d been admitted into hospital at the age of four with a concussion and a broken arm. There were notes of previous scrapes and bruises as well as a cut to her brow that had required several stitches. Dean surmised that maybe she’d been in some sort of accident, whether it be in a vehicle or otherwise. It was another question he would store away to ask her when the time was right. His stomach started to churn as he learnt these little facts about Y/N, the reality dawning on him that someone was very eager to keep the real facts about Y/N hidden. He turned the page, keen to learn more but quickly turned to Charlie when there were no more pages left. It didn’t make sense, most of her life was missing. 

"Is this everything? Because there’s nothing here past-”

“-past the age of six,” Charlie finished, slowly pulling out a chair to sit down next to the eldest Winchester, a sad smile on her lips.

“How can that be? Is there more you still need to find out?” Dean urged as his mind went into overdrive, the documents crumpling in his hand as he clenched them tightly in his palm.  

“I can keep looking but that’s all I could find so far. Someone has spent a lot of time and money to do this, Dean. That and they must have friends in  _very_ high places. Her entire record appears to be a cover up which means  _you_  need to tread very carefully,” she explained, running one of her hands through her hair as she frowned, “Y/N is definitely not who she says she is,” she continued, concern filling her tone.

Dean stayed quiet for a moment, his free hand coming up to rub at the stubble on his cheeks as he tried to think about this rationally. Someone didn’t want anyone to know Y/N’s true history and that was concerning. In his line of business, it could mean a few things. Maybe she was in witness protection, forced into this life to keep her safe or maybe the real Y/N Y/L/N was murdered long ago and the woman in his office was an imposter. All he knew at this moment in time was that his mind was feeding him endless possibilities and he needed to find facts, he needed strong hard evidence before he could confront her about any of this. 

“Have you found any digital footprints that could tell us who was behind this?” he asked Charlie, his voice still gruff, his hand still resting on his stubble as he looked over at the redhead who was shaking her head gently. 

“Not yet, but I can keep going,” she offered, “although I will say that I doubt it will be any of the low ranking mobs around here, they’re not that smart to pull this off. This is serious work.” Charlie’s face was one of concern as she waited to see what Dean’s next move would be. He took a moment to think things over in his head, of where to go next. He couldn’t be caught with his pants down again, things were just going right for his business so this time, he needed to be clever.

“Start with The Hemlock, that’s where she works, where she’s from. Maybe we’ll find something there.  Just…” he sighed, standing from his chair as he tucked the documents back into the brown folder, tucking them under his arm, “just keep going and don’t mention any of this to Sam, leave it with me.” 

“Dean,” Charlie worried, a little sigh passing her lips as she turned in her chair to face him as he walked towards the door. 

“I know but trust me, I’ll tread careful,” he reassured her, sending a small smile her way. “I need to play this smart, Charlie.”

“OK then. Just - watch your back,” she warned and Dean nodded, reaching for the handle of the board room door before making his way down the hall towards his bedroom. He had to hide this folder away for now until he knew what his next move would be.

As he reached his room, he ensured the doors were locked behind him as he found a place to hide the folder. Looking around, his eyes landed on his collection of vinyl records and stashed the folder between them before he collapsed into a sitting position on his bed. He loosened his tie from around his neck before running both of his hands through his hair, throwing himself back onto his mattress. He was confused and rightfully so. Y/N was an enigma to him. He thought he was finally getting close to her; he’d let down enough of his own barriers to let her in slightly so he thought she had done the same. But today was a reminder that there was so much he was still yet to learn, he’d been swept up in this surreal fantasy of a woman.  _His fantasy woman._  The woman he was  _paying_  for her to be. How could he be so stupid?

With a growl, he slapped the mattress either side of him in anger before sitting back up straight. Out of everything he’d learned, there was still one thing he couldn’t get his head around. Why did those records only go up to the age of six? Did the real Y/N vanish at that age? Had the real Y/N died and this  _imposter_  came and took her place? In his line of work, those ideas weren’t unrealistic, they were probable. With a frustrated sigh, Dean shook his head, trying to think of any other reason as to why, if she was the real Y/N, she’d been off the grid since she was six. Witness protection seemed to be the most viable option but he doubted she would have been encouraged to take a career as an escort. A career where she’d be in the public eye. But if she wasn’t in witness protection, what had happened to her? Surely she wouldn’t have been able to take care of herself and hack her own records at that age. Y/N was  _smart_ , but not that smart. So if he wanted to throw caution into the wind and believe that she was in fact the real Y/N, it just left him with one question.

Who the hell was she working for?

His first thought was to call Balthazar, throw him a few thousand dollars to persuade him to leak a few details but he knew that this would be bigger than an office worker. He thought to call Gabriel, who knew a little about everyone but then he doubted he would allow Dean to do business with anyone who could cause harm to his family. The only way Dean would get answers, would be to play the long game and ask the right questions, at the right time. His chest felt heavy at the thought of Y/N not being who he’d believed she was but in this life, you could never truly trust anyone. 

Standing from his bed, Dean decided to make his way back to his office, back to his brother and back to the woman who was meant to be helping them solve his parents murder. He was now questioning whether allowing her to work in his office was the best of ideas but with his little brother by her side and Charlie now being more vigilant than ever, he felt a bit more at ease.

As he got back to his office, his hand hovered over the door handle as he took a deep breath, painting a small, smug smile on his features before he pushed down the lever and opened the door. The sight in front of him, made his fake smile seem more genuine as his office was littered with evidence, theories and Sam with his nose deep in a book. He glanced over at Y/N whose head had whipped up to look at him as soon as he entered the room. 

“Hey, how did your meeting go?” Y/N asked him with a soft smile on her lips, stopping what she was doing to immediately to give him her full, undivided attention. Dean swallowed hard and forced a grin, shutting the door behind him.

“Safe to say we’re now in business with Abaddon,” he told her, his hands out wide in a boasting manner as he walked around to the couch Sam was sitting on; the couch opposite to Y/N. 

“That’s great news, Dean,” Y/N replied, her smile wide as she continued to beam up at him. Dean was going to find this harder than he thought to keep quiet. Turning around, he uncuffed his shirt sleeves and rolled them up his arms slightly, trying his hardest to focus on them and look as if he was acting natural. 

“Don’t get me wrong, we’re not her favorite people but she prefers us over Nick so for the time being, we’re at a truce,” he explained. 

“Can we trust her?” Sam suddenly asked, joining the conversation as he turned to look at Dean over the back of the couch he was sitting on. 

“For now,” Dean surmised, pursing his lips together as he rubbed a hand across his brow, his mind working overtime. 

“What was that with Charlie before?” Sam questioned and it made Dean’s mouth run dry. He took a chance to briefly glance over at Y/N who had looked back down at her laptop before he went back to his brother.

“Oh, she just wanted to run some tech stuff past me, nothing too important,” he lied. “So, you guys have been busy huh?” he asked, referencing to the room that was covered with notes, photos and any other bits of evidence that the two researchers had found. He circled around the couch to stand between the table and the cushions so he could get a better look at the makeshift layout of his parents murder scene that had been created on top of his coffee table. 

“Dean, I think we’re actually closing in on a lead,” Sam admitted, a hopeful look on his face as he glanced over at his elder brother. Dean’s eyes went wide at his confession. He hadn’t actually expected for him and Y/N to find anything so for them to think they have a lead was naturally shocking.

“Really?” Dean asked, a little perplexed as he looked between Sam and Y/N, waiting for one of them to explain in more detail. Sam looked over at Y/N himself and gestured for her to take the lead with the explanation, a reassuring smile on his lips as he did so.  Dean followed his gaze and looked over at her, his green eyes finding hers as he waited for her to start. 

“So, after looking at the photos and reading the reports, there are a few things to me that didn’t seem to add up, so me and Sam tried to recreate the murder scene,” she started to explain as she handed Dean photos of the footprints found at the scene of the crime. “Those footprints in the snow don’t correlate with your parents, meaning the assassin had to make his way down from his sniping point to check that they’d passed,” she continued, pointing to the spot on the makeshift scene on the table to reiterate her point. 

“Yeah, we knew that already,” Dean said flatly, letting the photo fall loose in his hand as he leant forward on his knees. He internally winced when he saw the flash of hurt that went through Y/N’s eyes, her focus now on the scene in front of her and not him. 

“But those footprints lead back to the main road and from the main road, there is only one way up to a possible sniping location. So, if we take that into account, along with the measurements of your parents vehicle which I then cross referenced with the tyre marks on the road and the angle of the bullet wounds; you got the sniping location wrong,” she told him, taking a deep breath at the end of her sentence as she offered a sincere but encouraging smile towards him. 

“What?” Dean asked dumbfounded. It was a lot of information to process in thirty seconds and he had to admit he was a little lost. All he could focus on was the fact Y/N had said that they had got the location wrong. Sam let out a little chuckle next to him, clearly amused at how lost his older brother had gotten with Y/N’s explanation. 

“What she’s trying to say is, we’ve worked out that there could have been another possible sniping location which the assassin could only get too by passing this particular hunting cabin,” he told him, pointing towards where the new possible sniping position was on the makeshift scene. 

“A hunting cabin which installed an outside security camera, a week before your parents were murdered,” Y/N continued, passing Dean some more photos of said cabin before she looked back over at Sam, waiting for him to take over. Picking up his laptop, Sam tapped a few of the keys and cleared his throat, handing it over to Dean. 

“I managed to get a hold of the security footage from that night and…well watch,” he told him, pressing the spacebar on his computer so the footage would play. 

Dean stared intently at the screen, watching the flickering footage from the cold night his parents had been taken from him. There was nothing for the first few seconds but when a security light came on after sensing motion, Dean’s eyebrows raised to his hairline as he saw a car drive past; the license plate number visible to the screen. He couldn’t help but replay the footage, not believing his eyes the first time around. However, seeing that car the second time blew him away; Y/N and Sam had actually found a lead, Y/N had actually come through and helped them become a step closer to finding out who did this. 

“I’ve ran the plates and apparently the car was stolen a month prior to this date, it was a high profile steal due to the customisation of the vehicle,” Sam explained, cutting Dean out from his thoughts even though his green orbs were still fixed on the screen. 

“We’ve just got to find out who stole it,” Dean thought aloud, his gaze flicking up from the laptop to his little brother who was next to him. 

“I’m going to put in a call to Crowley, see if he knows of anything,” Y/N announced, standing from her seat. “Could I borrow someone’s phone?" 

Before Dean could offer, Sam had already handed over his cell and Y/N took herself outside to the veranda, ensuring she was still in sight of the brothers. Watching her intently, Dean let out a long and low sigh, a calloused hand running the length of his face as he tried to process the past hour. 

“I need a drink,” Dean breathed, suddenly standing and making his way over to the makeshift bar in his office, “want one?” he offered Sam, turning slightly as he awaited the response. 

“Yeah, I’ll take a beer,” Sam replied, leaning back into the couch and resting his arm on the side. Dean didn’t waste time in pouring himself a double shot of whiskey, needing it to ease the manic pace his mind was racing. 

“It’s nice to see that you’re getting along.” Dean passed Sam his beer before he made himself comfy back on the couch. It wasn’t a lie, he was glad Sam and Y/N were being friendly, it helped them work well together to achieve what they had. 

“Dean, I didn’t hate Y/N, I was just very dubious about her intentions here. Especially considering what’s happened before,” Sam explained before he took a small sip from the cool beer bottle. 

“Are you still concerned?” Dean asked, his lips teasing the edge of his glass tumbler as he watched the youngest Winchester play with the label of the bottle. 

Sam sighed, “I’ve had Charlie keep an eye on her laptop since we’ve started and Y/N’s come up clean each time. She’s helped you, she’s helping with this even though this isn’t part of her job description…” 

“But?” Dean encouraged, sensing Sam had more say. 

“There’s something about her, Dean, something that I just can’t put my finger on,” he breathed, running a hand through his hair as he leant forward and placed his bottle on the table, “but she’s earned my trust.”

Dean knocked back his whiskey in one hit, the liquid burning the back of his throat as he let the words his brother had just said, sink in. Sam could sense there was something about her and he was never normally wrong. Should he tell him what Charlie had found? The words were already at the tip of his tongue, Dean so badly wanting to talk it through with his brother. However the thought of letting Sam down once again was more than he could take in that moment. Besides, he doesn’t know whether this was anything too serious…yet.

The sounds of the door opening from outside caused Dean to look straight at Y/N as she entered the room. All thoughts of spilling the truth pushed to the back of his mind as he took in the look on her face. 

“Guys? Does the name Azazel mean anything to you?” she asked, Sam’s cell phone in one hand, the door handle in another as she stared in the Winchesters direction, her voice wavering slightly with nerves. 

Son of a bitch. 

“Azazel?” Dean growled, glancing briefly at Sam. “Oh…we know Azazel alright,” he confirmed, his voice dangerously low as he slammed his glass tumbler on the table in front of him causing Y/N to jump slightly.  

“Well…according to Crowley, he deals with illegal vehicle imports.  _All_  illegal vehicle imports,” she spoke slowly, hoping that Sam and Dean caught on to her insinuation.  

“Sounds like us and Azazel need to have a little chat,” Dean spat, rising from his seat as he placed his hands on his hips, pacing his little allotted space back and forth as he tried to quell his anger. 

“…but he works for Nick right? How are you going to-” Y/N started.

“-we have our ways, Y/N,” Sam cut in, offering her a small albeit comforting smile as he held his hand out for his cell. “I’ll get Benny and Cas to scout out his location, then we’ll make our move,” he spoke aloud, aiming this thought at his brother who just nodded silently as he took in the news that Y/N had just fed him. 

As he paced, his green eyes glanced over at the woman who had made all of this possible. A part of him wished Charlie hadn’t told him anything until she knew absolutely everything there was to know, just so he could enjoy this moment with Y/N. But he knew Charlie was right in telling him when she did, especially with letting Y/N get so close to him. However as he looked over at her in this moment, he couldn’t deny the feeling in his chest as he watched her tuck some loose hair behind her ear, Y/N chewing nervously at her bottom lip. All he wanted to do in that moment was march up to her and use his thumb to pull down her delicious bottom lip before encasing her lips with his own. He needed a distraction, he needed to keep level headed for his family’s sake. 

“Well. I think a celebration is in order,” Dean suddenly announced, his sudden change in demeanor making Y/N jump slightly when he clapped his hands together. 

“What?” she asked, a little confused.

“We have a lead on our parents assassin, our mob has risen through the ranks once more and it’s all thanks…to you,” Dean told her, pointing towards her as he walked closer, smiling a forced smile. He noticed how she looked at him with worry, her body language changing slightly as he neared. 

“Dean, are you OK?” she questioned timidly, looking up at him from under her long lashes once he was next to her.  

“Peachy, sweetheart,” he husked, breaking eye contact with her as he cleared his throat.  “Come on, what you drinking?” He gestured towards the makeshift bar before grabbing his favourite bottle of whisky, pouring himself another double shot. 

“Same as you,” she replied to which Dean gave a single nod, pouring another helping into a fresh glass tumbler. 

“Beer or whiskey, Sammy?” Dean shouted over his shoulder, hesitating as he waited for a reply. When one didn’t come immediately, he looked over his shoulder to see Sam talking on his cell still. He picks up the bottle and shakes it towards his little brother causing Sam to stop and nod in agreement to the beverage. “Whiskey all round then.” Dean grinned.

For the next couple of hours, the Winchester’s and Y/N stayed in Dean’s office, drinking whiskey and talking about anything that came into their heads. Sam and Y/N were leading most of the conversations, Sam talking about how he got into law and what led him to choose that path. Dean was being a silent observer, getting a conversation started before backing out to just sit and watch. He chose to sit back down next to Sam after he announced the celebration, an action he knew would cause Y/N to question a few things. He knew he was being distant and that it was obvious but he couldn’t allow his heart to rule his head, not this time. 

As Dean sat there, he slowly watched his little brother’s and Y/N’s inhibitions lower, the alcohol in their system taking effect leaving them slightly drunk while he stayed sober. Unbeknown to present company, Dean hadn’t been serving himself as much as he’d been serving them, wanting to see if Y/N would slip up; if her tongue would become a little more loose. He knew it was a sly move but at this moment in time, it was the only unharmful thing he could think of doing to get information without asking her outright. She was now on her fourth glass of whiskey, her posture had become less guarded as she moved to lay horizontal across the coach, fumbling as she did so.  

“You’re such a lightweight, Y/N,” Sam laughed as she slipped, her empty whiskey tumbler being dropped onto the floor. “I didn’t think you would be considering your profession,” he continued, a teasing tone to his voice as he brought his own drink to his lips. 

“My profession, is to be whatever my client needs me to be, that means keeping a level head,” Y/N huffed, pointing her wiggling finger at the youngest Winchester as she tried to make herself comfortable. 

“Not so level now though,” Sam teased.

“I’m in good company, my job here is done,” she responded, matter of factly before realisation hit her like a freight train, her eyes going wide as she looked towards the Winchester that had hired her. “This is ok, isn’t it?” she asked, her tone less confident than it was before. Dean lifted his chin as he looked back at her, her eyes wide like a doe as she waited for his answer. He frowned slightly at the sudden change in her, he was the one that asked her to drink so why would she care what he thought now? 

“Fine, sweetheart but you sure you’re ok? You’ve only had four drinks,” he pointed out, “have you not drank this much alcohol before?” He leaned forward and rested his arms on his knees. There was a brief silence as they stared at each other, his green eyes searching hers for an answer that he was desperate to find. 

“Of course I have!” she exclaimed, pushing herself up into a sitting position once more, running a hand through her hair as she looked away from Dean. He wasn’t convinced, her body language mirroring the same language it did when he took her to Pam’s Pizzeria; back to the first time she’d ate pizza. 

“Then give me one drunk, embarrassing story,” he asked, trying to sound playful but the look he gave her told a different story. 

“I…I don’t really have one.” Y/N shrugged, playing with her fingers in her lap.   

“Not even from college?” Sam spoke up, intrigued as to where this was going, leaning forward himself to mirror his brother. Y/N just took a deep breath, looking between both Winchesters before she responded. 

“I always liked to look after my friends when they had too much to drink, ensured they were safe and sound when we got back to our dorms,” she explained, acting like it was no big deal before she reached for the bottle of whiskey that had been placed on the table between them, eager to refill her glass that she picked up from the floor. It was with this sentence that Dean’s alarm bells started to ring, remembering the conversation he had with YN about college back at the pizzeria, back when she told him:  _“I didn’t live in the dorms, I-I was at home, so food was always available.”_ She’d lied to him. 

“I thought you didn’t live in dorms. You said you lived at home with your parents when you were at college,” he confronted her with a sharp tone, a frown etched in his brow as he stared her down. 

“I…I d-did,” she stuttered, intimidated under Dean’s hard gaze. “When my friends were drunk I’d take them back to their dorms and stay with them then go home the next day,” she continued to explain but Dean didn’t reply, instead he let an awkward silence take over. 

He was suspicious, his gut telling him that something was seriously off with Y/N. He’d just caught her out on a lie, a lie that she struggled to backtrack from. However, her explanation could be justified. It could be that with the drunken state she was in, she was finding it hard to recollect certain details. Then again it could also be that she was hiding something from him, something that could be a danger to himself and his family. He just wished he could work out which one it was. 

“So how did you go from that to…this?” Sam asked respectfully, not wanting to overstep boundaries but also curious as to how she became an escort. Dean watched as she rolled her eyes. Not with attitude or arrogance but from how many times she’d been asked that specific question. Hell, Dean had asked her the same one after the successful meeting and deal with Crowley. 

“Shit happened, Sam,” she sighed as she stood, taking her now full glass of whiskey with her, “it is what it is,” she spoke softer, staring at nothing as her delicate fingertip circled the glass edge of the tumbler. Dean noticed how she became lost in her thoughts, how she’d retreated into herself as her mind played over something he was unaware of. He knew in that moment that she was hiding something, he just needed to figure out what it was. “How about we play some music?” she suddenly asked, her walls up once more as she headed towards Dean’s record player in the room. 

“You guys go ahead, I’m going to check some things over with the guys before tomorrow then head to bed,” Dean told her, swallowing the last of his drink before gently placing the tumbler on the table as he stood. Y/N sauntered over to him, her fingers walking up his chest as she looked at him with wide, seductive eyes. 

“Do you not want to dance with me?” she almost purred, swaying her hips gently side to side. It took everything Dean had in that moment to grab her hands and pull them away from him, placing them back down at her sides. 

“Not tonight, sweetheart,” he declined softly, swallowing hard when he saw the hurt that shone in her eyes. “Sam, make sure she gets to bed safely, get her some water yeah?” he asked his brother as he looked over Y/N’s shoulder towards Sam, to which his little brother just nodded in agreement. 

Looking back down at the woman in front of him, he gave her a quick, small smile before he leant forward and softly kissed her forehead. He couldn’t allow himself to do any more than that, not until his head had been cleared of this fog. He took a chance to look down at her one more time before he bid his goodnight and left the room, letting out a long, tired sigh as he shut the office door behind him. The look on her face near enough killed him in that moment. Rejection, humiliation, inadequence; he saw it all clearly written in her features and he was the one that caused it. His head and his heart were in two different places and Dean was finding it hard to walk the line. Where his head was concerned, he had to put his family first. Where his heart was concerned, he wanted to believe that Y/N was innocent in all of this. In reality, Dean knew that no matter what the cost, he had to keep his family safe. 


	21. Chapter Nineteen

**Notes for the Chapter:**

> Hope you guys enjoy the new add! Thanks so much for reading and for your amazing comments and love on this series, it keeps me going. 
> 
> Much love xox

Dean couldn't sleep. No matter how many times he tried, he just couldn't shut off. His thoughts whirring around his head. The sleep he did manage to get, was filled with dreams of Y/N betraying him in some way. The first one was a knife to his back, the second one she'd poisoned his drink and the third one involved her working for Nick, that dream showing her cuddling up to his side. After that, he decided enough was enough. He pulled on his jeans and an old grey shirt and headed down to his garage. There was only one thing he could to to clear his mind and that was to work on his beloved Impala. 

A few hours into early morning, Dean had already completed an oil change on his pride and joy. His head was tucked under the hood as he began to fine tune the engine, wanting to ensure that Baby could run as smoothly as possible. His distraction was proving fruitful, not one thought of Y/N had entered his mind as he allowed his greased up hands to tend to Baby's engine, he was one with his machine. So much so that he didn't hear his brother enter the garage behind him. 

“There you are,” Sam acknowledged, his soft expression turning into one of concern when Dean failed to turn around. He walked up to the side of Baby's hood, ensuring he was in Dean's peripheral vision before crossing his arms over his chest. “You're in here early, you alright?” Sam asked, raising his brows as he searched to catch the eldest Winchester's eye. 

“Yeah, just working on Baby here. Couldn't sleep,” Dean replied casually, not once looking up from the engine as he tightened some bolts, “makin’ sure she’s all fired up ready to go,” he continued, leaning up from the hood as he wiped an oil covered hand across his brow. 

“About that,” Sam started, uncrossing his arms, “we just got word from Charlie about Azazel’s location, we’re making our move.” This piece of information made Dean's green eyes snap to meet his brothers gaze. It wasn't information he was expecting so soon but with Charlie on the case, he wasn't surprised. He grabbed the oil stained rag that hung from Baby's hood and began to wipe his hands. 

“Alright, give me a sec to clean up and we’ll head out,” Dean breathed reaching for Baby's hood to close it, only to have Sam stop him in his tracks. 

“I think you should stay here,” he informed Dean, “the boys and me, we will cover this one.” The green eyed Winchester took a second before allowing his eyebrows to knit together in confusion. 

“...why?”

“Just in case anything goes wrong, which it shouldn’t, but no point in both of us being in the same place at the same time. Play it smart,” Sam clarified, his reasoning making perfect sense to Dean. He knew his little brother was right but he couldn't help but feel on edge at his suggestion. His protectiveness over Sam reaching new heights since the death of their parents. But he also couldn't risk being out in the field right now with what was swimming through his mind. Distractions caused death and he didn't want anyone's blood on his hands. 

“Fine, text me your location and keep me informed, capiche?” Dean reluctantly instructed, pointing his finger at Sam. 

“Will do,” the youngest agreed, clapping his brother on the shoulder once as he made his way towards the garage exit. Dean watched him walk, a strained and worried smile pulling at his lips as he screwed up the rag in his hand. Just as he was about to continue to work on the impala, Sam turned around, a slight playful grin on his face. " Oh and Dean? Don't go getting _distracted_ by Y/N, considering she's _very_ hard to say no too and all," Sam teased.  It was like a punch to his gut, the thoughts forgotten were flooding back into his mind. 

"No promises," Dean returned, a forced tight smile on his lips. 

As soon as Sam was out of sight, Dean’s face fell as he turned to lean against the impala. He took a deep breath to calm the noise in his head, his eyes scanning the car to figure out what else he could work on to take his mind off Y/N once again. The image of her with Nick from his dreams, the thought of her betraying him just like every other woman in his life bar his mother; it was all becoming too much. He wanted answers but he knew he couldn’t go in demanding them, not the way he was accustomed too. If he was wrong, he’d lose her trust; he’d lose _her._ But if he was right...  

Dean let out a low growl as the thoughts continued to whir around in his mind. He could feel the anger within him start to rise. His breathing became harder, his jaw clenched as his head slowly shook from side to side in an effort to quell everything from his head. But anger took hold. In one swift motion and with a thunderous roar, Dean had swiped his tools all over the floor. He stood there for a moment, letting his chest rise and fall with each deep breath he took to calm himself, his heart beating hard against his ribcage as he studied the array of metal that was strewn across the garage floor. After a few moments, he turned back to face the open hood of the impala, deciding in that moment that the car needed a fresh set of spark plugs and that he needed some answers, he just needed to decide on how to go about getting those answers from Y/N. 

-

Sitting at the end of her bed, her phone in hand, her finger hovered over the send arrow. Y/N had just finished typing out her last report to send to The Master, letting him know that everything was still golden with her client. But she was doubting herself, her thumb rubbing the edge of her phone as she thought back to the previous night. Dean had been off with her. She thought after the night they spent together, followed by yesterday’s shower antics, she was doing everything he wanted of her and more. Yet, after coming back from the meeting with Abaddon, he’d seemed closed off and unsure around her. 

At first, she’d put it down to what her and Sam were working on. Going over memories and evidence of their parents murder must have been tough for the both of them. Even so, she was hoping that Dean would have seeked comfort in her arms, that he would have allowed her to make him feel good about himself and to distract him for another evening. But then she thought it could have been down to Abaddon herself. She may have planted poison in his ear about her, using Dean’s past to manipulate him into not trusting her to screw things up for Dean later on down the line. However, that idea seemed ludicrous to Y/N, knowing that Dean wouldn’t be so trusting of the mob boss considering their already rocky relationship. Which then made her think about where she could have possibly gone wrong with him. Was she not sexy enough to keep his attention? Was she failing somewhere? The thought about not being good enough for her client panicked her. The thought about not being good enough for Dean Winchester _terrified_ her. 

She was still determining her feelings towards the eldest Winchester, trying to separate her head from her heart, but it was proving difficult. She’d never experienced something like this. She’d experienced clients who treated her well, clients who told her how beautiful she was and how they never wanted to let her go but something felt different this time. The way he became protective over her at the Gala, allowing no harm to come to her. The way he spoke to her, treating her like an equal and not someone beneath him. The way he allowed her the freedom to just _be._

With a heavy sigh, she sent the already written message to The Master. She couldn’t face telling him the truth that Dean may be upset with her. She could already hear the disappointment in his voice and she could imagine the punishment that would follow. Instead, she was going to be productive and try her best to get things back on track with her client. Whatever it took, she had to ensure Dean was happy with her. 

Standing from her bed, she slid the phone back into the drawer where she kept it hidden. Her gaze then caught by the underwear that she’d bought when on her shopping trip with Dean. It was a seductive set, a black lace bralette with matching laced panties that she was yet to wear. Glancing at the clock at the side of her bed, she knew it had been over an hour since Sam had left the manor, taking security detail with him as she’d watched them leave earlier in two Range Rovers. Assuming that he would be gone for a while, it was then that she formed her plan. She quickly pulled the underwear from the drawer and started to discard the clothing she was wearing. 

Taking a few moments to ensure the bralette and panties were in place, she strapped on a pair of black stilettos and grabbed her long mid thigh silk and lace kimono, threading her arms through the sleeves. She quickly glanced at herself in the mirror, grabbing a little bit of makeup to touch up her look before smiling with satisfaction when she finished. Tying the kimono around her waist, Y/N made her way out of her room with smokey eyes, red lips and a little bit of confidence. She was determined to find Dean, her first stop being his room but when she knocked a few times and there was no answer, she changed direction and walked towards his office. When her search there also came up empty, she decided to head to the kitchen, knowing how much he loved his food and was probably in there for an early lunch. 

Y/N’s heels clicked against the wooden floor, her arms wrapped around her middle as she gracefully walked towards her next destination, a smile firmly planted on her lips just incase she ran into the eldest Winchester. She'd be lying if she said she wasn't looking forward to seeing the look on Dean's face when he saw what was underneath her kimono. It had only been a day but she was already missing the feeling of his hands on her skin, his kisses upon her lips and his body pressed tightly against hers. Her tummy turned with excitement just thinking about it as she rounded the corner into the kitchen, her smile faltering slightly when she saw that only the Winchesters cook occupied the room. 

"Hello dear, are you hungry? Can I make you something?" Magda softly asked her, her kind eyes looking over at Y/N whilst she smoothed down the front of her apron, a warm smile stretching her lips. 

“Oh, no thank you Magda," Y/N politely declined, one arm tightening around her waist to ensure her kimono was tightly fastened. Even though Y/N’s intentions probably looked obvious, she didn't want Magda to see anything she didn't have to. “Have you seen Dean at all?” 

“When he last came here, he was covered in oil and grease. Smearing it all over my counter tops. My guess is he’s in the garage,” she chuckled lightly and Y/N couldn’t help but smile back at the elder woman. Her warmth seemed to radiate from her. Magda’s character one she would imagine a Grandma to be. She often wondered what a kind soul was doing working for a mob, with the work being so dark and dangerous but she knew that everyone had a story, just like she did. 

With a brief nod in thanks, Y/N turned around and walked towards the door that led down to where Dean was working. She used light footsteps as she descended the concrete stairs, not wanting him to know of her presence just yet, wanting to be a surprise. However, as she placed her foot down from the bottom step and rounded the final corner, the view in front of her made her mouth go dry. 

Dean Winchester was bent over the hood of the impala, his muscles tensing under his tight, oil covered shirt. She watched the way his biceps fought against the material as he flexed his arm, the way his brow was creased in concentration with his mouth parted slightly. He moved back to observe his work, a hand coming to rub at his chin before placing his tool down at his side. Y/N drew the corner of her lip up between her teeth, the sight in front of her impossible to resist, her body already aching with need for him. 

“Putting those large hands to good use I see,” she purred, slowly coming into Dean’s view from the doorway of the garage. He looked her way suddenly, his jaw slackening slightly as he took all of her in. She was walking dangerously slow towards him, one foot methodically being placed in front of the other as she swayed her hips. 

“She just needed some fine tuning,” Dean informed her, his voice more gruff than usual. He cleared his throat, tearing his eyes away from the woman who was sauntering his way to focus back on his car. It was clear to him that she had come in here with an agenda and after he brushed her off the previous night, he wasn’t too shocked. Surprised? _Definitely._

Dean had never stared so hard at the innards of his car, his eyes not really fixing on anything, considering he’d done almost everything he could think of doing to the impala. No, at this point he was staring to keep his eyes on anything other that the seductive woman who had just made it to his side. The woman whose gentle hands were slowly caressing his arm, her fingers twitching over his muscles as she slid them up to his neck, caressing the edge of his jawbone as she encouraged him to look at her. Dean closed his eyes, focusing on the tender touch of this enigma of a woman before taking a deep breath. He slowly looked at her, his heart pounding in his chest as he watched the fingers of her free hand undo the knot in her kimono tie.

“Y/N,” Dean breathed, his green orbs widening slightly as she slowly moved the fabric of the kimono to either side of her body, showing him exactly what she had on underneath. He was trying his hardest to think with his head and not with his heart, his previous thoughts pounding at the forefront of his mind stopping him from truly letting himself go. He couldn’t have sex with her, he couldn’t be this intimate with a woman that potentially could harm his family, no matter how he felt. 

He watched with lidded eyes as she leanned back against the framework of the impala, arching her chest just slightly to make her breasts that little more noticeable. Her hands were now at the edge of his shirt, her fingertips grazing his hard abdomen that twitched slightly under her touch. She leaned forward, her plump lips finding the pulse point on his neck softly, grazing her kisses along his skin. Once more, he closed his eyes before bringing his hands up to hold hers tightly against his stomach. 

“Y/N, stop,” his voice just above a whisper but the instruction in his words brought her to a halt. He slowly moved her hands from under his shirt and back down to her sides, his eyes not leaving hers the entire time. He saw how her brow furrowed and her body language changed towards him, her arms grabbing the sides of the kimono to cover herself as she looked down and away from him. 

“Have I disappointed you in some way? What am I doing wrong?” she pleaded with him, asking him so desperately as she studied the floor, too afraid to look at him. Dean felt the familiar guilt wash over him that he felt the night before when he left her standing in his office. He rubbed at his forehead, trying to think of a coherent answer that wouldn’t give the game away. 

“Nothing it's just…” he began, his mind then forming a plan as he took in the closed off woman in front of him. He needed to be smart, he needed to tread softly and so, that was what he was going to do. He took another deep breath; this was it. “Y/N, you’ve been here for nearly a month. I’ve seen you near enough every day and yet I don’t know a single thing about you,” he told her softly, a small sigh escaping his lips to fill the small silence, “tell me something, anything," he asked her, honestly, dipping his head down to catch her gaze. 

Y/N squinted her eyes at him slightly. “What does that matter?” she questioned, a confused scoff passing her lips as she shook her shoulders.  Dean could see that she was trying to work him out, he could see the suspicion that was written on her face, but he was desperate for answers. If this is what it took to get them, then so be it. 

“It matters to me,” Dean’s reply was honest, his voice steady as his eyes flicked between hers, waiting with bated breath to see what her reaction would be. This was make or break, his idea of getting answers to his worries without having to ask her outright. He just hoped it would work.

“Fine,” Y/N sighed abruptly, removing her arms from around her body. “My favouite colour is blue, I prefer long baths to showers and I think ghosts are real,” she listed off quickly as she once again reached for his clothes, desperate to pull them from his body. Dean frowned deeply at the sudden change of pace. Did she think he was joking? Has no-one ever asked her anything about who she really was? He shook his head, moving away from her once more and clasped her hands in his, only this time he took a more firm hold of her as his fingers wrapped around each of her wrists.

“No, Y/N, enough!” Dean stressed, bewildered by her actions; Y/N eyes wide. “Right now, I don’t care for your persona or who you pretend to be. I want to get to know you _._ The _real_ you,” he spoke softly, his thumb gently caressing the back of her hands as he urged her to let him in, to tell him _something._ Something that would tell him that what Charlie found was not a red flag. A moment of silence passed between the pair, her eyes cast downward at their hands as he felt the energy around him shift. 

“I’m really not that interesting,” she whispered, pulling her hands slowly out of Dean’s grasp and folding them around herself, ensuring to wrap her kimono around her frame as she did so. Her sight was set solely on the empty space in front of her as her mind started to whirl. Dean frowned as he noticed her dazed state, reaching for the rag that was hanging from the frame of the car to the side of him.

“You’re kidding, right?” he asked, a small disbelieved scoff following his question. But when Y/N didn’t reply, he looked back at her concerned. “Look, I’m not asking for your biography, i’m just asking for something. One little fact about _you_.” She didn’t answer and Dean noticed how her shoulders had sagged slightly, her earlier confidence nowhere to be seen. He needed to make this easy for her, he needed to get her to open up so he could maybe somehow find out information that could link to the records that Charlie had found. Pursing his lips, he played with the rag in his hands, his fingers pulling at the threads as he turned to lean against the impala next to her.  

“You know, back when I was younger, I was in this car accident with my dad and Sam,” Dean started to explain, his voice soft, “this truck came out of nowhere and slammed straight into the side of Baby here. I was in a coma for a while, Sam and my dad got out with cuts and scrapes but not me. My body struggled to cope and went into cardiac arrest but luckily, the doctors on hand saved my ass,” he finished, swallowing hard at the memory. He allowed a moment to pass, looking down at his twiddling thumbs as he waited for a reaction or response from Y/N but when no sound was made, he glanced her way. 

She hadn’t moved, her arms were still firmly wrapped around her middle and her gaze was still focused on the empty room in front of her. He continued to watch her for a few more moments, waiting to see if she would react at all to his gaze or to the heavy silence that had fallen over them; but nothing. He took a deep, long breath and shook his head, allowing a sigh to pass his lips quite audibly as he pushed himself off of the impala. He was irritated, he thought he could get through to her, he thought that if he told his story first, she’d open up to him and tell him something real. But who was he kidding? With a huff, Dean started to walk away from her, rubbing at his stubble frustratedly. 

“I was four,” her timid voice barely cut through the quiet but it was enough to stop Dean in his tracks. The frown on his brow disappearing as he turned back around to face her, her frame still huddled against his car. “I-I don’t remember much, just a lot of fire and smoke. There were people yelling and screaming. I was woken up by the loudest bang, it shook my whole room. There were flames everywhere and I was scared, I just remember being so frightened," she whispered, her arms tightening around her middle as if to give herself some comfort. Y/N swallowed thickly, shuffling slightly against the car as she took a shaky breath, "My mum and sister didn’t survive that night." 

Dean closed his eyes tightly for a second, his head hanging a little lower as he let her words sink in. Losing loved ones is hard enough but to lose them at that age...he couldn’t even begin to imagine what pain she must have gone through. What pain she may still be going through. 

“I’m so sorry, sweetheart,” he breathed, his words honest and true as he slowly made his way back towards her. She glanced his way briefly and he hoped in that small amount of time she looked him in the eyes, she noticed the compassion that laced his words. 

“Somehow that night, I managed to get a broken arm. I got away with a concussion, some cuts and bruises. Apparently, the stairs collapsed as I was trying to escape the fire, my arm got trapped under a wooden beam. At least that was what my dad told me, I can’t remember myself,” she mumbled, a frown etching her brow slightly as she tried to pinpoint her thoughts. It was a night that she had pushed to the back of her mind, the details of her injuries hazy. Dean sat back down next to her, inching closer to her side, his arm brushing against hers slightly in hopes that would bring her some comfort. 

“Is he still around, your dad?” he questioned, his voice soft and gentle. 

“Your guess is as good as mine,” she sighed, running a hand through her hair before rubbing at her forehead. 

“You’re not in contact with him?” Dean frowned, wondering why she would not keep in touch with the one parent she had left. It was obvious there was more to her story, more to what happened when she was younger and the long pause she was taking to his question clarified that. He didn't push her however, didn't urge her on to answer quicker. Instead he just sat and waited, his green eyes scanning over the side of her face. He watched closely as her brow twitched slightly, how her throat moved as she swallowed hard; how she moved and rolled her lips. It was obvious that this was difficult for her, her facial movements telling him that she was trying her best to keep her emotions at bay. She parted her lips and Dean took a deep breath, waiting on tender hooks for the words that were about to leave her lips. 

“After the accident, something changed in him. We were always moving around, going from one town to the next, we never really settled anywhere. Then a couple of years past and things got so much worse.  He started gambling, drinking, leaving me on my own in dirty motel rooms for hours on end. He’s a completely different person to me now,” Y/N explained, her voice just louder than a whisper. 

She turned to look at Dean and in that singular moment, everything clicked into place. Her records that Charlie had found hadn’t been hiding anything sinister, they had been hiding Y/N’s haunted past. He shook his head, feeling disgusted at the way her father treated her when she was so young before catching her gaze as his head stilled. His heart hurts for her as he saw the innocence in her eyes; as he saw the scared little girl that just wanted to be saved from the flames. 

“Did he do something to you, Y/N?” he asked her cautiously, his hand coming up to tuck some stray hair behind her ear, her eyes squeezing shut tightly at his touch. “What happened to you?” Dean waited for her response, hearing his own heartbeat thud hard against his chest.

“Doesn’t matter, it’s in the past. You learn from it and you move on,” she told him, shutting down the conversation before it could go any further. 

She pulled back from his hand slightly, masking it as a movement to pull at her kimono but Dean knew she was shutting herself off from him again. Her walls slowly rebuilding and her shield recharging, ready to fall straight back into her persona. He needed to change the subject, divert her feelings into something else to keep this honesty flow between them going. He decided to let her have a breather for a moment, walking over to the small cooler in the garage to grab her a bottle of water. In this moment, he felt a weight being lifted from his shoulders, the heaviness around his heart lightening as the fog in his mind began to clear. The injuries she sustained were from a house fire that ended in a devastating loss for her and he could only surmise that the reason her records stopped at the age of six was because she’d been taken into care, maybe witness protection to get away from her father. He wanted to push her further, wanted to find out exactly what happened after those few early years but if he did, it was possible that he could lose her entirely. For now, he’d take it as a win that the woman who captivated him entirely wasn’t the evil mastermind his mind was making her out to be.

With a bottle of water in hand, he turned back to face her, noting that she had moved slightly from her spot, her eyes wandering around the garage instead of being fixated in one place. It made him feel better knowing that she was becoming comfortable in her surroundings and with him, the topic of conversation hadn’t been an easy one and he appreciated that she was honest enough to tell him the truth. As he reached back to her side, he decided to keep things a lot more lighthearted and hoped that would keep Y/N from retreating in on herself.

“Would you mind telling me something else?” Dean passed her the water bottle as he asked his question, a small smile on his lips as she thanked him for the refreshment. She took a moment to take a long sip before nodding softly, mirroring Dean’s smile as she looked back at him.

“What do you want to know?” she queried and it took him a minute to think. He really wanted to know what happened between herself and her dad, he wanted to know just how bad it got for her but those questions would have to wait. 

“If you could do anything, anything at all in the world, what would be your dream?” Dean leaned back against the impala once more but this time ensuring he was closer to Y/N, his arm stretching around the back of her as he leant against the metal. 

“I..I don’t know, Dean,” Y/N answered, shrugging her shoulders slightly as she played with the cold bottle in her hands. 

“Bullshit,” Dean snorted playfully, his smile widening slightly, “everyone has a dream,” he continued, nudging her with his shoulder. The movement made her lips twitch, the corners turning upward as he waited. Only a few seconds of silence passed, his eyes never leaving her features as she thought about her answer.

“I’ve always dreamt about a little home by the sea,” she started, her voice a little timid as if she was scared to admit it out loud, “nothing fancy, just quaint. The sound of the waves crashing against the shore, the sea air; sand between my toes. Nothing for miles around. Just peace and quiet," she sighed, looking back at Dean to see a comforting smile on his face. However the moment her eyes met his, she looked back down at her bottle, shrugging her shoulders and shaking her head, "it's not much of a dream-" 

"-but it's your dream, sweetheart,” Dean cut in, his smile never fading as he pushed himself off his car to walk in front of Y/N, his index finger coming up to hook under her chin to encourage her to look up at him, "and if I’m honest, that sounds pretty damn good to me." 

The smile that Y/N gave Dean in that moment made his heart soar, it was soft but honest, like someone had just given her the biggest compliment in the world. 

“Yeah?” she asked, looking for that final clarification.

“One hundred percent,” Dean answered her quickly, his hand leaving her chin and slowly sliding down the front of her kimono, his finger hooking itself just under the edge of the material. “Although, in my version, you’d be wearing this _all_ day,” he admitted lowly, trying to lighten the mood. Now his mind had been cleared of worries, he wanted to appreciate all of her in any which way he could and he was going to start here and now. He knew she’d dressed specifically like this to please him and he wanted to let her know just how grateful he was and just how beautiful she really is. 

“Oh really?” she asked coy, dropping her water bottle to the floor as her arms came up to wrap around his neck, releasing the tie of her kimono as she did so, the material falling to her sides to show Dean everything that was underneath.

“Damn straight,” he growled, his lust filled eyes roaming her figure as she spread her legs slightly, pulling him closer to her before his lips slammed onto hers. 

He poured everything he could into that kiss. As his lips moulded around hers, as his hands clung at her hips, he wanted her to feel safe; protected. He wanted her to know that he would save her from any fire or danger that would come her way. He wanted her to know that he would spend hours listening to her tell him her dreams and her ambitions. He wanted to let her know that because of her letting down her guard, he’d let his down just a touch too. He wanted to get lost in her, the way her hands felt against his skin, the small whimpering noises she made when he brushed his tongue along her plump lower lip. He could spend hours being molded against her body, kissing every inch and worshipping every curve. 

However, the sound of a loud buzzing pulled him from his hazy thoughts, drawing him back to reality and making him catch his breath. It took him a moment to place himself but soon he remembered just who might be calling him. Reaching in his pocket for his phone, his other hand not leaving Y/N’s waist, his eyes widened when he saw the called ID. He wasted no time in answering the call. 

“Sammy?” He called, his voice low and gruff. He could hear the sounds of scuffling and muffled voices, the sounds of car doors and engines. He was just about to open his mouth to call his brothers name once more, fear creeping into his chest as he thought the worst when Sam cut him off. 

 _“We’ve got him, Dean.”_ The eldest Winchester’s eyes went wide at Sam’s confession, _“we’ve got Azazel and we’re bringing him in.”_


	22. Chapter Twenty

**Notes for the Chapter:**

> Ah guys. 
> 
> Sorry its took a while. Laptop broke, car broke...its been one on those kinda few weeks. However, I've ensured this new add is super long for you. Over 9000 words! I hope you enjoy...please let me know your thoughts.

 

It took a moment for Sam’s words to settle in Dean’s mind.  _ We’ve got him. _ Sam and the rest of the crew had only been gone for just over a few hours yet they had captured Azazel already. Different scenarios started running through his mind all leading to the same conclusion; this could be a set up. Immediately, Dean sprung into action, wanting to be ready just in case his suspicions became a reality. He quickly finished his call with Sam, hanging up and sliding his phone back into his back pocket before beginning to tidy up all of the tools that surrounded him, leaving Y/N standing concerned against the hood of the impala. 

"Dean?" Her hand came out to reach his bicep, offering a gentle squeeze as she encouraged him to look at her, "everything OK?" she asked him softly, a soft frown creasing her brow. Dean stopped in his tracks, his fingers squeezing tightly around the wrench in his palm.  

"That was Sammy," he started, briefly glancing down at her, "they've got him." He took a deep breath after he spoke those words aloud, hearing himself say them made it sink in all the more that the bastard that had a hand in killing his parents, would be here in his home soon.

"Really?" Y/N’s question was one of shock and Dean took a moment to ponder it as he threw the tool into his toolbox and shut it. Her reaction to the news giving his worries their validity.

"It seems too easy," he admitted, a small sigh leaving his plump lips as he ran a hand through his already unruly hair. 

"Or maybe you guys are just that good." She was trying to make him feel better and for that he was grateful but it wasn’t enough to quell the worries of an ambush from his mind. 

"Maybe," he uttered, rubbing at his forehead as he tried quickly to formulate a plan. One thing he did know however, was that he needed Y/N to be dressed in a lot more than she already was.  "Do me a favour, sweetheart? Go upstairs and get dressed, then meet me in the kitchen.” 

"Alright," she breathed, covering herself over with her black lace kimono as she proceeded to walk back towards the entrance of the garage. 

"And do it quickly," he instructed, his tone void of emotion as he gave the order. Y/N just nodded, hurrying her steps, the clicking of her heels on the concrete telling Dean the pace she was moving. He knew he sounded like a dick at that moment, barking an order at her instead of asking her but time was of the essence here. Sam was on his way back with Azazel and he needed to be ready for whatever shit storm may present itself. 

Picking up his tool box, he walked across the garage and placed it on the workbench on the far side, sliding it back into place. For a second, Dean thought that maybe he should change out of these clothes and be more presentable but then knowing what he was going to put Azazel through, he changed his mind. He didn’t want one of his best suits to be ruined when blood was spilled. He quickly checked his appearance in an old, oil splattered mirror he kept hanging in against the wall, ensuring his face was clean before reaching into the top drawer of the workbench and pulling out his trusty 1911 .45 Colt.  He tucked it into the back waistband of his jeans before walking back over towards the Impala to ensure it was locked and secured. With one final look around, he hit the light switch on the garage and headed back up the stairs to the main hall, his next destination clear in his mind. 

It was a few doors down from the garage, close to the back of the hall and hidden behind the back of the staircase. It was a room that Dean hadn’t had to use very often but it was one that in his line of work needed to be there as a necessity.  Some people would call it a dungeon, others would say torture chamber but to Dean it was a room of solitude. 

Pushing open the heavy iron door, the hinges moaning slightly under the weight, Dean reached to the side and flicked on the light. It flickered a few times, illuminating the room in flashes before it stayed constant. In the middle of the room was a singular chair, straps on both armrests and legs to secure someone in place. To the sides, were racks and racks of different interrogation devices. Blades, stun batons, steel knuckles, hammers; the list was endless. Everything you could possibly think of was in this room and he knew he was going to need them once Azazel arrived. 

Leaving the light on but shutting the door behind him, Dean left the room to head to the kitchen, eager  to join Y/N and have her at his side to ensure she was safe. Maybe it had been this easy to capture Azazel, maybe he had made a wrong move somewhere and forgot to cover his tracks but Dean had to question all these possibilities. If it was a trap, just how did Azazel know that the Winchester brothers were coming for him? It seemed far fetched, knowing the only answer to his thoughts would be that there was a mole amongst them but he knew in his gut, that wasn’t the case. At least, not after his talk with Y/N. She’d calmed his wandering thoughts by allowing him that tiny glimpse of her past. 

As Dean got closer to the kitchen, the sound of tyres on the gravel driveway made him snap his head to the front door, the wide windows either side allowing him the view of his brother and the rest of the crew pulling up. Quickening his pace, Dean popped his around the door frame leading into the kitchen and caught Y/N’s eye. He quickly brought his finger to his lips, and motioned with his head for her to join him by his side. If this was a trap, he was going to play it as safe as he possibly could.

Y/N quickly and quietly rushed over towards him, his large hand coming to wrap around her wrist gently as he tucked her body slightly behind him, his eyes trained on the front door. He heard the heavy footsteps on the gravel as the engines of the cars cut out, soft murmurs bleeding through the walls as his crew grew near. His right hand was etching closer to the gun tucked in the back of his jeans, readying himself for anything that may come his way. 

When the front door swung open, Dean relaxed slightly when he saw that his family and friends were safe and Azazel was bound by cuffs with a black bag over his head. Benny was the one that was marching the captive into the manor, Cas hot on his heels to be on hand in case he was needed. To Benny’s left was Sam, a pistol in his hand as he nodded greeting towards Dean. 

“You alright?” Dean immediately asked, giving his little brother a once over as he got closer. 

“I’m good,” Sam confirmed before motioning towards Azazel with his gun. “This is him.” 

Dean’s gaze fell onto the hooded man standing in front of him, his eyes narrowing slightly as his face became stoic. He nodded once towards Benny, an indication for him to remove the captives hood as he took a deep breath in preparation for what was yet to come. It only took Benny a quick second to remove the black hood from Azazel’s head, the captive blinking violently as his eyes adjusted to the bright light in the Winchester’s foyer. However, it wasn’t long until his eyes focused on Dean, the eldest Winchester locking onto his gaze and holding it. 

It was a long minute, silence engulfing the room as the atmosphere grew tense around them. The stare down between the two men seemed to go on forever, neither of them breaking, neither of them speaking. They were sizing each other up, both of them looking for tell tale signs of weakness on the other, both of them trying to figure each other out. However, it was Azazel that broke first, Dean’s hardened stare proving to be the most dominant as the captive’s eyes took in everything around him, until they finally landed on Y/N. 

"My, my, my,” he breathed, running his tongue over his rough, chapped bottom lip, “what a pretty little thing you are," he leered, his eyes roaming over her figure. 

"Hey," Dean snapped, moving to stand in front on Y/N protectively as he continued to stare down the enemy in his manor. Almost immediately, Azazel’s face fell flat as he snapped his attention back onto the eldest Winchester. 

"What's up, Deano? Momma never taught you to share your toys?" he taunted, a small smirk on his lips as he tilted his head to one side. Dean’s jaw ticked slightly, his lip curling before he balled his fist back and thrust it forward, straight into the captives stomach, making him recoil where he stood. “Ah, that's alright,” Azazel wheezed, fighting through the winded feeling,  “see, she was my little plaything first. We had a grand old time," he taunted, his breathless jibe causing Y/N to gasp audibly. 

"I don't know you!" she exclaimed, instant worry painted on her face as she desperately looked between Dean and Sam. 

"Oh you do, doll face, you must certainly do," Azazel chuckled, sending her a sly wink. 

In the matter of seconds, Dean had pulled the gun from the waistband of his jeans and in one swift motion, collided it with the side of the captives head, rendering him unconscious. He couldn’t listen to his vile words any longer, or put up with seeing the way he was obsessing over Y/N. He turned slightly to see her standing next to him, her arms loose by her sides as she stared back at Dean with wide, pleading eyes. She wanted him to believe her, that she had no involvement with his prisoner but Dean wanted answers and he knew for damn sure that one way or another, he was going to get them. 

"Take him downstairs," Dean grunted, sliding the gun back into the waistband of his jeans as he watched Benny and Cas nod in submission to his order. It was only when Dean had watched them drag Azazel towards the readied room, that he turned back to face his brother. "Sammy, don't let Y/N leave your side till I'm back, understood?" he asserted and waited for Sam to nod in agreement. With confirmation from his brother, Dean turned and began to follow the steps of his crew, determination in his steps and a simmering anger resting behind his eyes.  

Y/N watched on until Dean was out of sight, a panic building up in her as she tried to mentally process what the hell had just happened. It was true, she had never seen this man before in her life. The first she had ever heard about him was when she was helping to research the death of John and Mary Winchester. What game was he playing? Was Azazel doing it to just wind Dean up? Did he know that she was an escort and not  _ actually  _ Dean Winchester’s new love interest?  

Her thoughts were cut short when she felt a large hand wrap around her arm, a gentle force leading her into the large sitting room to the side of her. Sam quickly let her go, closing the double doors behind him to ensure they had some more privacy. Y/N couldn’t help but think the worst; that Sam didn’t believe her either. She watched with wide eyes as he moved around the room, placing his gun on an end table before shedding himself of his jacket.

"Sam, I swear I've never met that man before in my life," she began to explain, panic lacing her words as she held out her hands in front of her, "please, please believe me!" she pleads, her mind in overdrive. This was another thing The Master would punish her for, if the Winchesters didn’t kill her first.  

She watched on as Sam ignored her pleas; as he pulled up his sleeves to his elbows before he slowly stalked over to her. Y/N held her ground, unsure of what her next move should be. She swallowed hard as Sam got closer, slowly releasing a shaky breath as he brushed against the side of her. She heard the sound of clattering wood, the sudden invasion of noise making her jump slightly as Sam walked away with what looked like two pool cues in his hand.

"W-what are you doing?" she stammers, confusion now flooding her mind as she stared at Sam walking towards the pool table that had gone unnoticed by her at the side of the room. 

"What's it look like?" Sam replied, a small smile on his lips as he held the cues separate in each hand, lowering one slightly in Y/N’s direction, hinting that she should take it.

"Pool?" she asked, slightly bewildered at what was happening at that moment. She thought for sure that he was going to threaten her yet here he stood offering her a pool cue, waiting for her to take it. "I don't understand," she told him quietly, timidly stepping forward to take the long wooden implement from his hand with caution.

"Humor me." Sam raised his eyebrows as he waited for her answer, a small nod of agreement coming from Y/N. She watched as he set up the coloured balls on the bed of the table, wondering just what the hell was going on.     
  
-

Tightening the last strap on the armrest of the chair, Dean ensured that Azazel was secure before grabbing the jug of ice cold water that had been placed on the side thanks to Benny. His hand firmly wrapped around the handle, he pours the liquid over his captive, his lips already snarling as he waits for Azazel to rouse. Seeing how he was only partially becoming conscious, he threw the jug to the side and grabbed the smelling salts instead, firmly grasping at Azazel’s jaw before he wafted them under his nose. Eventually getting the reaction he wanted, Dean slapped his face hard a few times, helping him come around quicker.

“So handsy,” Azazel mumbles, his snarky comment not going amiss by the eldest Winchester. Already fed up with his bullshit, he grabs at his face once again and forces the captive to stare up at him.

“Listen here you son of a bitch, you best start talkin’ and telling me what I want to know,” Dean demanded, his tone dangerous as he threw Azazel’s head back out of his palm. 

“Not even gonna offer me a drink first?” Azazel snides. Dean’s lip twitched before he pulled back his fist and quickly punched Azazel in his face, the sound of impact echoing around the room. “Guess not,” he quips, spitting out some blood that had appeared in his mouth. 

Dean curls his nose up in disgust, turning towards his metal tray as his green eyes gather over the array of tools he has at his disposal. His first choice was a long serrated blade. He ran his finger along the metal, flicking it over the edge slightly and smirking at the sharpness. Turning back around, he faced Azazel as he swayed the blade in his hand, getting a feel for the weight of it and allowing his mind to form a plan. 

“Am I supposed to be intimidated by this?” Azazel taunts, blood still seeping down his lip but his arrogant smirk was still present. Dean just huffed a single laugh, air pushing from his nose as he looked down at his captive before he placed the blade on the prisoners bare forearm, slicing open his skin painfully slow. 

“Oh...I’m just getting started,” Dean spat, placing the blade on Azazel’s opposite arm as he repeated his actions. Dean could see how he tensed, how he gritted his teeth together to save him from screaming out. 

“Please,” Azazel started, “who are you trying to fool, Dean? Yourself? Your  _ darling _ girl up there? You’re just a boy pretending to be a man,  _ trying  _ to fill his dead daddy’s shoes,” he taunted, a slight chuckle to his words as he looked around the room. However, Dean wasn’t a man to stand for insults nor was he going to stand for his games any longer. Another keen smack to Azazel’s cheek made the chair rock slightly from the force, his head snapping to the left with it.  

“Shut your goddamn mouth," Dean warned, speaking through clenched teeth, his hand gripping the handle of the blade painfully tight. 

"Oh, I've hit a nerve." Azazel smirked before allowing his mouth to drop open, fresh blood seeping from his lips. 

"I want to know who killed my parents," Dean started, his tone dangerous and low, his eyes dark and menacing. "Now I can carve you up, piece by piece, until you're barely breathing or you can tell me who killed them right now," he seethed, bringing the blade in his hand to Azazel’s cheek, digging the metal into his flesh slightly. 

"Come on then, kid, give me your best shot." 

-

Y/N took a deep breath as she lined up her shot, Sam had offered her the break so she accepted. With a strong push, the triangle of pool balls scattered in every direction, her Y/E/C eyes quickly scanning every moving object to see which ball potted first. Colours or stripes. Finally, the sound of a resin ball being potted was made and Sam looked down to announce that she’d be playing the colours. She knew he was watching her every move intently, each precise shot that she made offered her some sort of approving nod from the youngest Winchester. 

"You're pretty good at this, Y/N,” Sam complimented, leaning on his cue as he watched Y/N pot her fifth ball, leaving her with only two more colours to pot before she could move on to the eight. 

"You learn stuff over the years," she murmured, still feeling uncertain with Sam’s intentions but her mind was becoming more at ease as she focused on the game at hand. She moved around the table, her sights set on her sixth coloured ball as she bent low to aim her cue and line her shot. 

"So, Azazel..." Sam started, causing her shot to miss her ball considerably. 

"Sam, I've never seen him before in my life," she told him once again, looking up at the youngest Winchester with wide eyes as he stood close next to her, his eyes scanning the pool table as he mentally prepared his next move. 

"Why should we believe that?" Sam asked, his tone dangerously calm as he left Y/N’s side, walking around the table to face her, rubbing the end of his cue with some chalk. 

"Well I-" she started, pushing herself up into a standing position, her hands resting on the side of the table. "I've tried to do the best I can for you whilst I've been here. I've used every skill I've ever learned to help get you guys here. Believe me, I would never take away the opportunity for you to get your revenge on your parents killer. You and Dean need that closure," she explained to him boldly, her eyes never leaving his. Sam took a moment to study her before allowing the tiniest smile to grace his lips, the acceptance of her answer. 

"You care for him, don't you?" he questioned, bending lower to aim his cue at his first striped ball. 

"Dean? I care for all my clients, Sam. That's my job," she replied, cautiously, unsure as to where he was going with these questions. 

"Cut the bullshit," he retorted, potting his ball before standing up straight. "Finding out who killed our parents wasn't part of your job description. We only needed you for the Gala. You could have gone back home but instead you chose to stay. Why?" he asked, shrugging his shoulders loose as he looked for his next move.

The question threw her and she took a moment to think it over, watching as Sam lined up his second shot. It’s true, she didn’t have to help them with their parents death, she didn’t need to be still there with them but she couldn’t tell him the truth that she was terrified of going back to The Hemlock. She couldn’t tell him the reasons behind why she was terrified. 

"Dean…he’s been nothing but kind to me through all of this,” she admitted. It was the truth, not the whole truth but it was true enough to answer Sam’s question. 

It took Sam a moment of thought, his eyebrows knitted together as he thrust his cue forward, successfully potting his second ball. Y/N could see that he was mulling her words over in his head when his eyes connected with hers and his frown deepened.

“Are your clients never normally kind to you?” His question made her heart jump and her stomach turn. She thought she had been clever, she thought she hadn’t given anything away. Sam watched her closely, pausing the game a moment to wait for her answer.

“Yes, sort of,” Y/N explained, looking down at the table and the mess of balls upon it, “Dean’s the only one that’s treated me like a person and not an asset,” she told him softly, her fingers coming up to play with the hair at the nape of her neck when she felt the slightly raised bumps of her tattoo, the mark The Master made her have as soon as she turned twenty one. She was grateful that her hair hides it so well, especially knowing that Dean wouldn’t believe her if she told him it didn't mean anything or that she got it drunkenly one night after college. 

Sam let out a long breath as he once again lowered for his shot, distracting her from her thoughts as a silence took over them as he potted his third ball. 

“That sounds concerning, Y/N,” he spoke truthfully, looking up at her with worry etched in his features. 

“No! No,” she panicked, blurted out her objection quickly which caused Sam to raise his eyebrows at her outburst. She had to correct his thoughts, he couldn’t know the truth, “I mean it in terms of he’s wanted me for more than what I can do in the bedroom. Not putting sex in our contract, not wanting me at his side of every second he’s awake. It’s just a...refreshing change. I just wanted to return the kindness, that’s all,” she explained, hopeful that her words had convinced him otherwise. 

Sam just nodded and offered her a soft smile, his eyes going back down to the pool table as he looked at the amount of balls he had left to pot. He hadn’t given anything away to her, whether he believed her or not about Azazel or about her clients and it had her slightly on edge. She was in enough trouble as it was back at The Hemlock and if The Master found out she’d blabbed about how well she was treated, she knew she wouldn’t see daylight for a very long time. All she could do at that moment was hope that she’d done enough. 

-

“Is that…” Azazel started, breathless, “is that all you got?” His taunts were still strong considering the amount of pain Dean had been putting him through. 

Throwing the used and bloodied blade to the side, Dean let his eyes roam over the tray as he decided on the next weapon he was going to use. He needed something painful, something more effective than just slicing his skin with a knife. When he spotted the hammer and a box of nails, he smirked and allowed his large hands to pick them up. Turning around to face Azazel once more, Dean hardened his stare on his captive as he pulled out one large, long nail; only to hear him laugh. Dean paid no mind to it. Instead, he lined up the first metal pin on Azazel’s thumb knuckle and without hesitation, smacked the head of the hammer on to it, driving it through the bone and into the wood. 

“You’ve got a serious temper simmering under your skin there, boy,” Azazel half chuckled through his whimper, “how much is going to take to  _ finally  _ make you go  _ boom _ ?” he spat, trying to mask his pain through anger. 

“Ten knuckles, ten nails,” Dean said, his voice gruff as he ignored the question and lined up the second long nail on the next knuckle. “Who killed my parents, Azazel?” One swift motion meant that the second nail was hammered once more into bone, attaching the captive to the chair beneath him. Blood trickling from the wounds, down the leg of the chair into a neat pool next to Azazel’s feet. 

“Tell me, how are Ellen and Bobby doing these days? Is it business as usual?” His breathing was unsteady as he continued to taunt Dean, his eyes the tiniest bit hazy. It took a second but it was then that the eldest Winchester realised that Azazel was behind the boutique and garage getting trashed and set a flame. 

“You and your boys, huh?” He was angry but his voice stayed deceptively calm as he reached for the third nail and lined it up once more, hammering down fiercely into the wood. “Business is booming actually, your plan kind of sucked on that one. Molotovs were pretty weak,” he informed Azazel, reaching for the fourth nail and hovering it over his fourth knuckle. “Now, who killed my parents?!” 

When the captive didn’t respond, Dean huffed and drove the nail through his skin and bone once more. Azazel’s screams filled the room, the blood that was dripping from his hand steadily increasing with the four nails that were impaled through it. Azazel rolled his head from side to side, grunting and groaning before his eyes landed back on those of Dean’s. 

“Let’s talk about that  _ beautiful  _ woman you have upstairs shall we?” Azazel started, his words coming out more breathless than before. Dean just took a deep breath, turning to reach for the fifth nail from the box. The captives' eyes followed the green eyed man’s movements, wincing slightly when he felt the tip of the nail rest against his little finger’s knuckle. “Tell me, how good is she in bed? When all this is done with, I’ll get her to suck my cock until her mouth is sore,” he taunted, his smarmy laughs mixing with his screams as the fifth nail became embedded into his bone.

“Who says you’re walking out of here?” Dean asked, a smirk resting on his lips as he stared down at the blood that was steadily pooling around Azazel’s left foot. “You think you’re going to get rescued? Nah, see while you were unconscious, I made a plan. I have a man placed at every possible entrance, a team that works my security cameras, motion sensored turrets activated and scouts conveniently placed. I’ve got eyes and ears everywhere, your time’s up,” he informed his captive, pointing the head of the hammer at Azazel’s face. 

Dean noticed how Azazel’s lips started to snarl with anger, his one hand that wasn’t nailed to the chair starting to clench and struggle. The eldest Winchester knew he was getting somewhere, he was slowly working him down; he just needed to up the pain to get his answers. He reached for a sixth nail, pinching it between his forefinger and thumb before he shook it at Azazel in a taunting manner. He moved to place it over the thumb knuckle on the right hand, only this time instead of hammering it down, he tapped it just hard enough to piece Azazel’s skin but not hard enough to go all the way through.  _ Tap. Tap. Tap. _

“I’d ruin that pretty face of hers, that soft skin. Imagine it blistered and scarred, I wonder how it’d turn under the heat of a flame,” Azazel hissed and something inside of Dean snapped. 

“You’re not going to touch a fucking hair on her head!” he roared, swinging the hammer hard until it collided with the captives ribs, the sound of crunching bones mixed with screams echoing around the room. However, through the pain, Azazel continued to taunt, enjoying how easy it was to rile Dean Winchester up. 

“It’d be  _ so  _ nice to see her burn. Her skin bubbling and melting under a fire I created...just like the rest of them,” he laughed, manically. The blood from his lips dripped onto his chin and chest as he did so. Dean just stood back and frowned slightly, 

“The rest of them?” he barked his question, his gut churning as his green eyes focused on the crazed man in front of him. Azazel stopped laughing but his grin remained. 

“The houses that went up in flames, the screams of the people he wanted; the times i’ve stood back and admired the orange waves that wipes out those that don’t fall into line,” the captive recounted, a smug grin painted on his blooded lips. 

It was that moment when Dean felt two worlds collided. The sadistic look on Azazel’s face, the words he muttered to Y/N when he entered the manor; the story he just recalled that second. He was behind all of this. 

“It was you.” Dean dropped the hammer to the floor, his eyes never leaving those of Azazel’s. “That’s how you know, Y/N isn’t it? You were the one that set fire to her home!” Dean shouted but Azazel didn’t answer, he just maliciously grinned up at Dean. “You sick son of a bitch, there were children in that house!” he bellowed, his roars bouncing off of the walls around him as he got dangerously close to his captives face. 

“Beautiful isn’t it? Shame she got away,” Azazel almost sung, the wind being knocked out of him when Dean punched him in the stomach. He pulled back, his patience limit reached as he pulled his gun from the waistband of his jeans. He didn’t even give any warning, no threats were needed; Dean was done. With a quick flick of the safety button, Dean had aimed his pistol at point blank range on Azazel’s left kneecap and pulled the trigger. Blood splattering across the floor, bone fragments like splinters digging into Azazel’s own flesh. Dean was deaf to his screams. 

“Who...killed...my...parents?” he demanded, pronouncing each word slowly as he pressed the muzzle of his gun into the fresh wound, twisting it as he spat his words. At this point, Azazel’s breathing had started to quicken, his voice becoming like gravel as he snarled up at Dean. It appeared Dean had found his breaking point. 

“He didn’t listen to me, I told him how poetic it would be to watch your fuckin’ parents burn. I could have rigged their car to blow, I could have trapped them in that pass and doused them in fuel, dropped a match and watched them suffer. There were so many options but no, my way was too messy,” Azazel spat, saliva mixing with the blood on his chin, “I had to wait, with a fucking sniper rifle and just-” he made the noise of a gun shot with his mouth, popping his lips, “-at the right time.”

“You fuckin’ asshole!” Dean roared, taking his gun to Azazel’s other knee, blowing it just like his left. Dean didn’t even flinch as the bullet ripped through his captives skin. He didn’t flinch when a bit of the blood splattered onto his hand. He just kept his hardened green eyed stare on the bastard in front of him. Despite the pain he was going through, Azazel was still able to pant out his words, his eyes glinting with madness.

“Wasn’t  _ that _ good a shot though. Your momma, she was dead by the time I got to the car but your daddy? Oh...he was suffering. Appears my bullet didn’t enter his brain at the right angle...allowed him to bleed out just that little bit longer,” he snarled. 

_ Boom. _

Just like that Dean exploded, his rage blinding him for a brief moment as his roars shook the room. He reached behind him for the serrated blade he used earlier before spinning back and roughly placing it against Azazel’s neck, his free hand forcibly pinning his captive back against the chair by his jaw. 

“There it is!” Azazel praised, his words slightly slurred due to Dean’s tightened hold on his mouth.  “Your fury, your anger. You fucking Winchesters are all the same, you’re just worthless. You think you’re so in control when in fact, you’re just as messed up and fucked up as the rest of us yet you’re too chicken shit to do what needs to be done. Just as chicken shit as  _ poor old  _ John Winchester in those final moments, just as chicken shit as you will be when you find out what’s in store for you. He’s coming and he’s going to wipe you all out,” Azazel spat, fighting hard against Dean’s tightened grip despite the fact he was bleeding out all over the Winchester’s floor. Dean didn’t react to his words, the green in his eyes lost to the dark rage that was clouding him as he pushed the knife harder onto Azazel’s neck. 

“And just who might that be huh?” Dean growled, the metal of the blade slowly sinking into his captives neck. 

“Like you don’t already know,” Azazel scoffed, a smug look resting on his face as he took laboured breaths. 

“Nick.” Dean didn’t have to play a guessing game and at this point, he didn’t understand how it wasn’t painfully obvious that Nick was behind this before. 

“We have a winner,” he sneered. “He will bring you to your knees once and for all, Dean, you fuckin’ pathetic piece of-” Dean had heard enough, he pressed the metal hard against his neck and in one fluid motion, his slide it across his skin. Slicing through each layer of skin, muscle and vein until he was such he’d gone deep enough. 

He stood back as he watched the life from Azazel drain from his eyes. The blood, flowing like a crimson river down his captives chest, spilling onto the floor. Dean watched him twitch, he watched him gargle and struggle against his death as he faded away. He would stand there until he was sure that he wasn’t able to come back from this. Not that he would be able too but Dean wanted to be there when Azazel took his last breath. He’d got a confession from him. He had found out that Azazel had been the one behind Y/N’s childhood trauma. He needed to ensure that Azazel’s games were over. 

Once the gargling had stopped, and Azazel’s body became still, Dean turned around and made his way to the makeshift washroom that was situated to the side. A small little round mirror and a bowl with some hand wash and water was enough to wash away Azazel’s blood that has splattered onto his skin. As he rubbed at his hands, he looked up and caught his reflection in the mirror. The feeling of nausea bubbled in the pit of his stomach as he swallowed hard. Torturing wasn’t his favourite thing to do, hell, he’d hire someone else to do it if he could but he just didn’t know who he could trust. He wouldn’t want to put this kind of burden onto his little brother, he wouldn’t want him remembering the sights and sounds of someone bleeding out. His father always told him to do whatever was necessary to get the results you wanted. He’d even made him watch a few times when John used to be the one extracting information so he could learn a thing or two. Still didn’t mean he had to like it.

Drying his hands, he turned back and took one last look at the limp body occupying the chair before he reached for the handle of the door. Exiting the room, he nodded at both Cas and Benny who were standing outside on guard, letting them know the job had been done and for them to take over and clean up the mess. 

\--

Sitting on the couch, Y/N waited for Sam to join her, one foot tapping against the floor. After Sam’s questions, he had completely thrashed her at the pool, potting all of his balls on his only turn. She was shocked, not expecting him to be as skilled as he was at the sport. When Sam saw her reaction, he just chuckled, telling her to  _ ‘never trust a Winchester when it comes to pool’  _ before taking her cue from her and offering her a drink. 

Feeling the couch dip down next to her, she turned to see Sam holding two glasses of whiskey, one outstretched in offering to her. She took it graciously, offering her thanks as she stared down at the amber liquid that was softly swaying in the glass. Silence fell over the pair, Y?N’s focus was still on the contents of the tumbler in her hand whereas Sam was sipping gently at his beverage, studying the woman next to him. 

“I believe you,” he announced, breaking the silence between them, his fingers playing with the edge of his glass. 

“What?” Y/N asked him, shocked, her attention now on the man beside her. 

“About Azazel,” he began, “I believe that you don’t know him,” he told her, leaning back further into the couch to get himself comfortable. 

“R-really? That means a lot, Sam, thank you,” she gushed with relief, feeling like a small weight had been lifted from her shoulders with his words. She was still concerned by Azazel’s words, not understanding how he could know her but knowing that Sam believed that she had no ties to him, made her feel better. 

“I must admit, when Dean first brought you here I honestly thought he’d made a terrible mistake. Especially with what had happened before but,” Sam paused, looking over at Y/N to offer her a warm smile, “it turned out better than I could have hoped.”

“I’m glad, Sam. I’m glad you’ve got the business you need, the deals and everything. I’m glad that I’ve helped that way.” 

“Not just with the business, Y/N. With Dean too,” he told her, causing Y/N to look at him, the look she gave him encouraged him to continue. “It’s nice to have my brother back. He was so hellbent on pressing the self destruct button after Cassie, he didn’t realise how it was effecting everyone and everything around him. You’ve changed that to,” he explained, bringing his whiskey to his lips to take a large sip. 

Y/N took a moment to process what Sam had just said and she felt a warmth radiate in her chest knowing that she had helped Dean back to his old self, even if she hadn’t realised it until now. When she first met the eldest Winchester, she thought she was going to hate being here and hate being with him. She thought he was cocky, arrogant and was going to be over her like a dog on heat. But she was wrong. He was kind, caring, considerate and put everyone else before himself. 

She thought back to the Gala, the night Duke had handled her so viciously. Dean had stepped in twice to protect her even though he had only known her for a few weeks. There was the look in his eyes when Nick stood in the place where his father should have been; anger, grief, loyalty to his family. Then how could she forget the meeting with Cassie herself. Dean may not have told her in so many words, but he had been cut deeper than any knife could manage by that woman. The way he squared his jaw, the way his fingertips dug deeper into her hip as he pulled her closer, the way his eyes glossed over slightly through pain and anger. Dean Winchester was definitely not the man she assumed him to be on the first night. 

“What happened...with Cassie?” Y/N asked softly, leaning forward to gently place her whiskey on the coffee table in front of her before turning to face Sam once again, “if you don’t mind me asking of course.”  

“She broke him.” Sam let out a long, heavy breath, finishing the rest of his drink before leaning forward himself to mirror Y/N’s position, the tumbler loose between his fingers. “He fell in love with her, wined her, dined her. Did everything a man should do for his girl and then she betrayed him, betrayed us all. Took valuable documents of ours that had locations of our hideouts, our deals - basically everything. She took them and sold them to the highest bidder, sleeping with whichever mob boss would have her. Turns out, she was playing the long game and was working for Zachariah,” he scoffed, anger simmering under the surface of his words.

“...and you didn’t kill her?” Y/N asked him shocked, her mind reeling at the information Sam had just given her. She knew with mobs like these, any snitches of any kind were usually  _ dealt with  _ immediately so she was shocked to see that Cassie was still breathing. 

“Believe me, I wanted to. I still do but I was more concerned for my brother and keeping this family safe.” 

Y/N didn’t want to ask any more questions at this point, she didn’t have to enquire more as she knew by Sam’s body language and how he spoke about the situation that the subject was still raw. She knew it must have been an incredibly difficult situation for him without asking. Dean was in love with a woman who betrayed him, betrayed his family. You can’t switch those feelings off overnight, Dean wouldn’t have been able to deal with Cassie and they had a business to repair.  

“If it’s any consolation, from what I’ve learned from this job, the bitch will get what’s coming to her, eventually,” Y/N remarked, trying to offer some little comfort to the still angry Winchester. 

“I know and so does she after your confrontation with her at the Gala,” he told her with smirk to which Y/N could only blush slightly.

“Oh, you heard that?” A little chuckle left her lips as she watched Sam nod and grin widely, clearly finding the situation amusing. After the laughter had died down and a moment of silence fell over the pair, Y/N reached out to him. “I’m sorry she did that to you all, Sam.” 

“Don’t be sorry, just don’t be the same person she was and hurt my brother. That’s all I ask,” he said, the tiniest smile still on his features as he looked at her. 

“I...I wouldn’t,” she stammered, stunned slightly by his words after they’d been having such a deep conversation but she knew it was from a place of love for his brother, that she could understand. “Besides I go back to The Hemlock tomorrow,” she said with a sad smile. 

“You alright? You don’t exactly sound thrilled about going back home,” Sam worried, dipping his head slightly to try and get a better look of her. 

Y/N would give anything to tell them the truth, to tell them just how much she didn’t want to go back to The Hemlock and continue this life. She wanted to stay there, with them and live her life. She wanted to stay with Dean. 

“I’m just going to miss you guys, I’ll miss Dean. I’ll miss all of this. This has been my favourite contract to do so far,” she admitted, playing with her hands as she stared at her glass on the table. 

“You sound like you’re never going to see us again,” Sam half chuckled but concern grew in his features as she didn’t reply to him straight away. 

How could she tell him that he was right? That she would probably never set foot in this manor again? She knew that once she was back at The Hemlock, behind closed doors and prying eyes, her life wouldn’t be worth living. The Master will ensure that she’ll never get to work with Dean again, not after she broke so many rules. He’d be blacklisted, banned from the establishment and if she was ever to get caught with him, it would be the end of it all. 

As Y/N looked up from her hands to reply to Sam, her eyes caught the sight of the opening doorway only to see Dean Winchester enter the room. His shirt and jeans were bloody yet she could see no injuries, his face was solemn as he looked at noone in particular and Y/N yearned to throw her arms around him. She knew he’d hurt Azazel, that much was very obvious but just what had Azazel done to him?

Sam noticed her stares and turned quickly in his seat, his brow raising as he saw his brother standing there. 

“Dean?” he asks worriedly, standing up and rushing over towards his brother. “ Hey, you ok?” He checks for injuries but Dean just shrugs him off, walking over to where the whiskey bottle was residing and filling himself a glass. 

“I’ll give you guys some space,” Y/N announced, standing almost immediately after. She offered them both a small smile before she hurriedly left the room, allowing the brothers the privacy they needed. 

It took a moment for Dean to register that Y/N had left the room and that his brother was standing next to the couch, looking concerned. The events of the past few hours were whirring around his mind, Azazel, his parents death, Ellen and Bobby; Y/N. It was all one big blur.

“Dean?” Sam prompted, a frown upon his face as he stared at his older brother. Dean turned to face him, downing his glass of whiskey in one before pouring himself another one. He slowly walked over to the couch, his green eyes connecting with Sam’s. 

“That bastard killed our parents, Sammy.  _ He _ killed them,” Dean fumed, shaking his head as he still tried to come to terms with it. Sam’s back straightened immediately, his face becoming stoic as she stared down at Dean. 

“He admitted it?”

“Eventually. But it doesn’t end with him,” Dean started, taking a long sip of his whiskey as he walked around the couch, falling back into the cushions. He rolled his head to face his little brother whose eyebrows were raised, waiting for the rest of Dean’s sentence. “Nick.”

“N-nick?” Sam stammered, not believing what he’d heard as he came back around the couch to settle next to his brother. Dean still didn’t like this whole situation, his gut telling him that something wasn’t quite right somewhere. 

“It’s all too easy, Sam. Capturing him, the information he was giving out. Now I know I’ve got some skills when it comes to extracting information but that...it’s all too convenient for us,” he worried, expressing his concerns.

“Maybe we just got lucky.” Sam shrugged but the motion made Dean scoff. The Winchesters never just ‘got lucky’ and he feared that this situation was exactly the same. 

“Or maybe it’s part of a bigger plan,” Dean spoke aloud, drinking the rest of his whiskey as his mind whirred with his spiralling thoughts. “We’ll need to hold a meeting and work this all out,” he told Sam, reaching forward to slide his glass along the coffee table, licking the remainder of the liquid from his bottom lip. 

“What about Azazel?”  

“He’s dead.” Dean’s response made Sam’s eyebrows raise as he made a small scoff.

“And you didn’t think to come and speak to me first!?” Sam’s exclamation was expected, Dean knew that as he leaned his head back and squeezed his eyes shut. He knew he should have spoken to his little brother before he ended Azazel’s life but would the outcome have been any different? Sam would have wanted him dead just as much as him except at least this way, his brother had no blood on his hands.

“Sammy, he killed our parents...the stuff he was saying about them. He was the one behind the hit on Bobby and Ellen...Y/N…I just, I snapped alright?” he told him, a long sigh leaving Dean’s lips. 

“Y/N?!” Sam asked, a little confused, his tone calmer than before. The eldest Winchester ran his hands down his face, staring up at the ceiling as his head rested on the back of the couch, the cushion nestling around his head. 

“He took out a hit on her family when she was a child, set fire to her home which caused an explosion. She lost her mom and sister because of it,” Dean informed him, shaking his head slightly at the thought. 

“Shit, Dean,” Sam gasped, “that’s how he knew her?” 

“I don’t know, man. How would you recognise her from the four year old she was when he set her house on fire?” he asked his little brother, hoping for a relevant answer from him, anything that could stop his mind from running at a million miles an hour. 

“Maybe Nick and Azazel were keeping tabs on her throughout all these years for insurance,” Sam suggested, a slight shrug in his shoulders. He seemed too calm about this for Dean’s liking, surely his little brother could see how off this situation was?

“What if they’re still keeping tabs on her? What if they now kill her because of me?” Dean worried, the idea that she could be seriously hurt because she’s been a big part of his life for the past month, because she’s helped them bring her parents killer to justice. By killing Azazel, had he just signed Y/N’s death sentence? 

“You need to talk to her about this and you’ll need to be quick, especially with her leaving tomorrow,” Sam advised, clearly seeing the torment that Dean was putting himself through. However at Sam’s words, Dean’s eyes sprung open, his stomach churning at the thought of Y/N not being under his protection anymore; at her not being with  _ him  _ anymore.

“What? Tomorrow?” he sat up straight, running at hand through his already tousled hair. “Shit, it completely slipped my mind,” he admitted, rubbing at his neck as he tried to put his thoughts into order. Sam could see that his big brother was in turmoil over what to do for the best, this new information he had found out about her playing heavy on his mind.  

“No matter what, she has a right to know who took away her family,” Sam advised him and all Dean did was nod his head, understanding that he had a point. “Besides all that, are you really ready to let her go?” At Sam’s question, Dean turned his head, a small frown resting in between his brows. 

“What do you mean?”

“Dean, come on, I’ve seen how you look at her, how you are with her,” Sam mentioned softly, a knowing look on his face as he stared down his brother. 

“She’s good for business, Sam, that’s it,” Dean clarified, his frown not leaving his features.“She may have won us clients, won us deals and helped sort out my shit but that’s all it is. There’s too much I don’t know about her.”  

“I call bullshit,” Sam stated matter of factly, the look on his face not changing as Dean continued to stare back at him. 

“Really?” Dean scoffed. “Charlie found out some stuff about Y/N yesterday. Her  _ real _ records don’t go past the age of six. The records that we found were all fabricated, it takes some sort of technical mastermind to pull that off, Sam. Y/N’s good at what she does, but she’s not that good. Now this with Nick and Azazel?” The eldest Winchester just shook his head slightly, rubbing at his stubbled jaw. 

Sam could see why his guard was up, why he was looking into every single detail but he could also see that his feelings ran deeper for Y/N. She was no longer just the escort he hired to help with the business, she was much more than that to Dean now and it was obvious to everyone around him but himself. He knew the reason why Dean was refusing to let her in, why he was looking for any possible danger at any turn. 

“She’s not Cassie, Dean. You can lower your guard,” Sam advised him, as gingerly as he could. 

“Don’t you say her name in this house again, you hear?” he growled, pushing himself off of the couch to walk around. Sam held up his hands in surrender, but his concerned eyes followed Dean as he moved. 

“I trust Y/N, and you should too,” Sam suggested, standing from his seat as he lowered his hands and put them into his pockets “It’s your last night with her, Dean. Don’t be an idiot.”

On Sam’s last words, Dean stopped pacing and turned to face him, the youngest brother offering Dean a small, soft smile before he left the room. The eldest Winchester just stood in place and stared at the spot his brother once occupied as he let his words sink in. The fact that Sam would trust Y/N and tell him so, meant a lot to him. It was like an acceptance of her into the fold, a blessing from his brother that he should pursue whatever feelings he had with Y/N.

He slowly walked back over to where the bottle of whiskey was located before picking it up and bringing it back to his empty tumbler on the coffee table, filling it with the amber liquid once more. Was his brother right? Were his feelings towards Y/N more than just lust? He appreciated everything that she’d done for him, the lengths she had gone too to ensure it all ran smoothly and they got the deals the needed; to get where the Winchesters should be once more. He admired her courage to be bold when needed; the brief glimpse he saw of that fire inside of her back at the Gala made his lips twitch upward. He respected her work ethic, how dedicated she was when she applied herself to any one task and how well she would research a role before seeing it through. 

He sipped his glass of whiskey, appreciating the burn in his throat as he thought back to the time when Y/N was sitting on this couch with him, enjoying a similar beverage. She’d just helped renegotiate a fresh deal with Crowley and she’d teased the shit out of him; he knew there and then she’d be the death of him. He loved the innocence she carried considering the type of job she did. The way her eyes lit up when he took her to Ellen’s boutique and she had the freedom to design her own dress. The sounds she made when she tried her first piece of pizza; how grateful she was about it all. He loved that she opened up to him, that her dream was as simple as it could be. It wasn’t about money or power, it was just about simply  _ being  _ and he just wanted to be there with her. 

It was then Dean realised, his feelings ran a lot deeper than lust. 

  
  


**Notes for the Chapter:**

> Eeeee
> 
> There we have it. Please let me know your thoughts if you have time, thank you so much for reading!


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